And if it were set up where everything went through a title company so the buyer pays the title company, they manage the buyer's loan (from me), and the title company ensures my mortgage is paid without my direct involvement... what parts of the transaction would feel risky or not worth the headache to you? 

In fact, for tax sales in PA, the parcel number check is usually best performed first, to see what mortgages can be found (if any); seeing a big mortgage means it's best to move on to the next property on the list.And on a side note, IRS liens can be wiped out at foreclosure of any kind, provided the IRS lien is in a junior position and provided that proper notice is served upon the IRS. 

If you have a road maintained by the HOA then set aside for that in reserves. 

I would set the cleaning fee for at least what it costs If you feel the cleaning fee is high get some other quotes 

Also, bookkeeping needs to be set up. 

Then, after booking, I send a more detailed version to cover important details like noise, extra guests, and check-out procedures.Since you're in a vacation market, setting clear expectations upfront while keeping the details for later might be a good balance.

In order to do this you need to have deal flow and you need to know 1) How to recognize a good, profitable deal, 2) How to put together funds quickly to buy the deal before someone else does and in such a way where you are protected and the deal is protected, 3) How to run the project so that you follow the budget and don't overspend or overbuild, 4) How to attract an end buyer or a renter and which documents to use to protect yourself and the buyer, 5) If you are going to keep the property then you need to know how to set up the property from the start to best help you in the refinance later, and 6) You need to know how you are planning on managing the property from the beginning in order to make sure it will be profitable at the end.

We've used LLCs by going to sunbiz.org, setting up the LLC, and then heading over to IRS.gov to get the EIN (Tax ID) number.

That pain could take the form of working long hours, putting other aspects of your life aside for business, or uprooting your entire life for a short period to escape the rat race.

Save the low rate: Keep your current loan and focus on building savings for the next down payment through budgeting or a side hustle.2.