I have a bathroom attached to it, so I was planning on keeping it with the garage so I will end up just adding a small kitchen, living room/bedroom.

With those stats, you'll pull half the accountants in the forum out of the woodwork, most of us would be more than happy to work with someone in your financial position as it means we can provide a fair amount of value.Whoever you work with, I would recommend you consider finding a firm with substantial experience to offer in both real estate, and estate/gift planning given your goals.. 

Make sure to reach out to one with real estate experience, as location is not a problem these days.

~Have the owner make you the primary user and they are just the admin of the listing.

Same goes for the high-end markets you mentioned above.  

Of course there are more high-end platforms that are higher cost (Salesforce, hubspot) but I would not start there.

Hey @Barry Taggart from my professional experience pushing a close isn't a big red flag-- especially if it is a good deal.

Keep in mind that about 40% of the population rents.I agree with you that buying a run-down property requires experience, the biggest concern is that you don't get enough discount for the condition.

As I’ve just had a very bad experience with a contractor, is there a contractor contract template that someone would be willing to share? 

She updates my books twice a month.Try to find one who has real estate experience.