Additionally, I negotiated that the seller do a new exterior paint job ($20k), $6,500 in landscaping, and $5,700 in deck work to transform the exterior to attract new quality tenants.

A $50K house is not going to be in a nice area or attract quality tenants.

Over the the episodes from the past two weeks, David from the BiggerPockets podcast has brought up that real estate will be harder and harder to from the "small guy" to get into each year due to factors like: inflation, hedge funds being hyperactive in the market, the lack of supply and high demand causing an increasingly competitive market, real estate being a more attractive investment for our current economic condition, etc... 

Yes, I agree that any needed maintenance work is just needed and expected (roof, mechanicals, etc) and not substantially change any values, so to focus on what may attract good tenants and higher rents (adding a deck or dishwasher, etc.). 

The property is also in a very attractive location, within walking distance to the downtown area, and has an extremely rich history as it is was the historic town hospital. 

In my experience, if the rental income doesn't attract an investor at the price, you won't even get any bites from the investor pool. 

I've owned a bunch of waterfront property, kind of an attraction for me, on rivers, creeks, stream, and others close by. 

It sounds like you're close enough to town that if you get a social media following you can attract a lot of people.

Alternative :: do a DSCR loan in your name on purchase based on sale price and rents appraiser says, reduce HELOC request amount to what parents can get approved alone.

Creative and optimistic folk with great attitudes are attracted to RE, which is both our strength and our weakness.