A lot of the popular areas in Charleston proper that are not licensed under the old laws now require the owner to live on the premises to obtain an STR license.

You could form an LLC and have the operating agreement that allows your boss to require you to purchase his membership interest (or allow you to purchase his) in a given time frame.

Both these properties have mortgages and they both are required to have insurance on them.

You might covenant no water sprinkler systems or require them to put in a Cistern well system. 

Mainly the panel is in the basement and it would require a ton of work and paying for labor hours + repairs. 

However if you had done a warranty deed (or a special warranty deed if you still have a mortgage on it) instead, your LLC has a claim against you for the issue on the title, and you in turn can go back to your initial title insurance to fix it.Some title insurance will allow to transfer the coverage to an LLC that you own 100%, but not all of them do or they may require an additional fee.

However, one nice thing about this community is a one-time cost and it doesn't require additional payments.

My advice is to require them to pay the full balance upon the next payment.

A car forum that I'm a part of, and I know the owner of the forum, told me that the dedicated app required constant work and updates as phones and operating systems changed. 

In short, I can afford the additional $1100/mo cost of a second house, even until I rent it out.I have around $35K in HYSA and emergency funds that I could use for a down payment, but that's less than 20% which would be required for a conventional loan, assuming full purchase price.