It’s a big decision and shouldn’t be taken lightly…because you are right- it’s going to take time, effort and money (by way of loans/debt) to get that MD/DO.

Getting help from a TAS has definitely helped us in the past on addressing something like the IRS seeming to lose a payment and being unwilling to put the effort into finding it - nothing technically complex about your problem from what you are saying (just a lost payment), but if they aren't helping you, the TAS helps light a fire under them. 

Definitely very hot markets Inventory is light right now in Buffalo NY, but it has been a great cash flow market for years. 

Local realtors put out videos reacting to some of the horror stories landlords have lived through as well as recent law changes pertaining to the topic.Non-RE related... perhaps something that shows you in a more personal light... highlighting a restaurant you went to, a new workout routine or supplement you're trying, a book you're reading, hobbies/activities you engage in, etc.

If you were going to do something cool with that floor space like make space for weights, yoga, meditation or something of that nature it could be a good use and a reason to then go with a daybed, but you'd need to know that that is something your ideal guest avatar is looking for. 

I would start with some light cosmetic jobs and get those base hits. 

USA made light oak set for the breakfast nook, $50.

Full guts of the bathrooms, replacing all fixtures, throwing modern tile finishes for the tub/shower, new vanity, new cabinets in the kitchen, island, new stainless-steel appliances, new flooring throughout, new recess lighting, and likely new siding on the property to give it a more freshened pop for when it goes back on the market.

This is why talking to the wrong people can set you back light years in real estate investing.You are rushing the process from your post.

Your experience and resume of recent deals has more weight than your personal financial position.