Under "has the roof been replaced or repaired" there is a "yes" and under "has the roof leaked under your ownership" there is a "yes". And the description for these yes answers is that the heating system flashing was repaired.

Of course we will be having an inspection done on the house. But would something like this indicate there will be considerable roof issues with this house throughout our ownership? Is it typically a "deal breaker" type issue? Or is it easily repaired and likely the repair the owner did will be the last we hear of this?

Thanks in advance for your thoughts!

Flashing, in my opinion, is not a deal breaker issue. It's normal to need to maintain flashing periodically and a relatively easy fix. The hardest part is probably getting on the roof. This is kind of soon for a repair to be made and leads me to think it was a construction error. The bigger problem would be if other construction mistakes were made throughout the house. In other words, was this a minor mistake or is it indicative of the overall building quality?

An inspector can best answer your questions.

Most of them could not recognize deficient work if it hit them in the face.

Pay a roofer.

Preferably an old fart roofer that has been doing it for a long time.

The life expectancy of many of the 'new' methods has yet to be verified.

Their sole purpose is to reduce cost, and quality and life be damned.

What I don't understand is why you should not use a roof or home inspector recommended by your Realtor as a blanket policy that chispa stated.
I do understand that some Realtors do get referral fees from preferred vendors of all sorts, and that might be a conflict of interest if the Realtor were steering you towards those vendors and away from others. The Realtor should always disclose this to you, but you should ask just in case.
But a professional Realtor will have your best interests in mind and will recommend an inspector because he is one of the best, easy to schedule, reasonable rates, very thorough, provides an easy-to-read PDF report via email within a day or two, and used him for their own home purchase(s)! (applies to home, roof, seawall, and WDO inspections)
It is not a conflict of interest for me to recommend "my" inspectors to my out-of-town buyer - it's their choice to use my recommendation or find their own. If they choose their own, I will (of course) accompany that inspector, and if I like them and their product, will add them to my recommended list.

We put an offer in yesterday so I want to be prepared if we are able to reach an agreement.

It is not as likely to be an unbiased opinion.

How many RE folks would continue to recommend a 'deal killer'?

you really want an uninterested, uninvolved, does NOT stand to benefit either way, person.

Someone more likely to be objective.

I'm not sure WHO a "deal killer" is, but it's not a person. The inspector writes what he sees and it's up to the buyer whether or not if a newly discovered problem is a "deal killer". A professional inspector, the type that I would recommend, simply calls it as he sees it. I would absolutely expect him to reveal a major problem if one surfaces - that's what he's paid to do.

And they all require payment up front because they don't want people to refuse payment later because they don't like what they read in the report - does that sound biased or intending to benefit either party?

LOL. Our home inspector refused to go up on the roof. Probably because there was a foot of snow on the ground and he didn't bring a ladder.

How does one go about having a roof inspected in bad weather?

If I were the OP, I'd take a look in the attic and see if you can see any water dripping, or look for signs of mold or moisture. Perhaps your inspector could use one of those thermal cameras to see if he can detect any moisture behind the walls.

A person who points out insignificant defects and beats down every place would be a 'deal killer.'

There ase plenty of them out there.

raining for 'home inspector' is all over the place from state to state.

Some places license, others do not.

Anyone who wants to be a 'home inspector' can hang out a sign and start 'inspecting.'

There are even mail order courses.

Many point out electrical ad plumbing issues' that are completely code compliant, since the applicable code in almost every case is what was in effect when the structure was built.

NOT the latest revision for things built now.

Also, inspectors get business from realtors. It's a fact of business life. Some inspectors will minimize issues to get along with the realtor in the interest of future business, and some will not. Get referrals. Take your own pictures.

I always thought I should get two basic inspections, with $100 bonus to the most detailed. But it turns out I needed so many special inspections - chimney, oil, septic, well, lead, radon, asbestos, mold, all of which seem to be extra now.

Good luck.