However, chances of making a mistake or overlooking an opportunity to save are higher when it comes to rentals.The dilemma is whether it's worth paying a professional in this case.

@Ken Almira don't buy a Florida condo w/o checking that they've passed their engineering inspection and their reserves meet the new requirements.

These people often don't understand lending and have a checklist of boxes to check.

Even towns of less than 10k, as long as it is in a "good part" of town and there is somewhat stable growth in that area, then most lenders will not add any additional underwriting guidelines, especially if it is rented out.I always like to do the Walmart check (kind of what you recommended being by a store).

Check with local realtors for handyman recommendations. 

Check AirDNA for demand, pricing, etc.The Dekalb Board of Commissioners has proposed regulations for short-term rentals. https://engagedekalb.dekalbcountyga.gov/airbnb-dekalb-countyShort term rentals require you or your property manager to be hands-on and come with more risk.

Say home improvement and they will send you up to $50k at relatively low rates with no pre-payment penalties and they do not check how you spend the funds.

I just came across the idea, but don’t quite understand how it works or if it would be worth pursuing.

Once Apartments.com is going the money comes without much thought. i check on the first to see that the transaction has initiated then again on the eighth to see that the money deposited.

And with an HOA handling maintenance, have you checked their reserves?