If you go with the partnership route1) You need to manage the money going in and out of the business bank account.2) File a partnership return and be responsible for issuing K-1's3) make distributions to you and your partner for cash flow that you receiveYou will likely spend many hours on a nice gesture.I may want to consider instead to give a christmas gift or a bonus for early completion of projects.

Given his spending habits during his first term, it might be a wash.Costs to build new properties will probably increase.

Very responsive and great market knowledge! 

However, the biggest con is that you are sacrificing a bit of your privacy by living right by your tenants and it is usually a lot more stressful since everything is your responsibility - managing tenant issues, handyman repairs, taking care of the lawn, etc.I would strongly recommend house hacking especially in the Columbus Ohio market!

Let's cut to the chase:  "A tenant is obligated to follow HOA rules, as they are considered residents of the community and must abide by the same restrictions as homeowners, even though they do not own the property; the landlord is responsible for ensuring their tenants understand and comply with the HOA rules. 

The property ended up being his book keeper's home that she had rented out and was needing to sell.

No if potential buyer have given you emd than you are under the assumption this is a serious buyer and will close on the deal but he has only a certain amount of time with his inspection period so if he backs out you still have time to fund another buyer. 

I agree with both responses @Chris Magistrado.

That person is responsible for anyone one else that comes into contact with your property.I suggest using a service like Mayistay.

For the son to qualify for the $250k exclusion, I believe he would most likely need to meet the ownership and use test, meaning he needs to own and live in the home as his primary residence for at least two of the last five years before the sale.