⭕those $50,000 properties that could be rented right away with no repairs needed (no longer exist in this market lol)   I would like this chat to be experienced investors only. 

The real key is deciding whether or not you want to own the existing asset long term. 

I'll give you a few good ideas on what to ask, but the best thing you can do to ensure you're dealing with a credible lender that is committed to your success is to talk to other investors who have already worked with that lender.  

Hi BP,I'm looking to purchase a 2-4 unit owner occupied property in an A/B neighborhood in the capital region of Upstate NY. How many hours/week would it take you to manage a property like this on your own? What techn...

Been there, done that.....Now you can keep the existing ground level garage and install new structure above to carry the new load.

@Caleb BurkyI'm assuming you are speaking about the subject to or buying a home that is subject to an existing mortgage where the buyer agrees to make payments on the seller's mortgage.

Some other alternatives that may exist in your climate would be furring the exterior shell out, Adding a continuous Rockwool insulation shell, and then creating another layer of exterior siding.

The existing/inherited tenant doesn't sound like he's complaining, so much, as he is letting you know what needs to be done in his unit. 

I don't love the idea of paying PMI or extra fees, and the first lender I've gotten pre-approved with doesn't even do FHA loans, although I would probably shop around before committing to a mortgage anyways.

@Cordell Critchell In @David Krulac's book, he mentions some great tips about developing rural ground, like trying to use the existing roads, instead of paving your own in order to save money while splitting the land.