I am not yet familiar with the management fees for an STR yet as we self manage, however Cleveland itself is currently STR friendly and just requires them to be registered if you have stays over 90 days and then you register with the city and pay $35.

We do a small fruit basket and 2 bottles of wine (1st one complimentary, 2nd one, there's a "pay envelope" $10).BUT nothing says welcome to Eugene, Oregon like a couple of joints... :-)(just kidding, but depending on the Guests demographics, we can direct them to the best dispensaries...)

Your son is likely paying more than the property is worth, by definition, as the seller would almost certainly prefer a similar offer that was not subject to. 

I decided to buy the property from my grandfather using a gift of equity, which allowed me to take over ownership without having to come up with the full down payment and pay for the tax lien and his closing costs.

Plus, it integrates seamlessly with accounting tools like QuickBooks, making bookkeeping much more straightforward.Whichever account you choose, look for one with no monthly fees, online banking, and features like automatic bill pay.

Option 3: Pay large down-payment on modest rent ready house. 

Used funds to pay other debt off plus out cash in the side.  

And particularly one that pays but a fraction of their real job. 

The original six month tenant I had extended the lease 9 times and stayed a total of 5 years, paying me about $15k over market rent annually.  

So, you can do a land contract for 12 months, which should allow lender to credit you full value of the land vs the purchase price, but the loan will pay off the land contract, so the lender maintains first lien position.Can't help you with the rest of your question, but you should be able to search for "CPA" here on BP to find experts to reach out to.