The country simply does not have enough affordable housing units, and the new supply of affordable housing units is not keeping up with new demand.

It might be best to simply go to a local REIA networking event and meet some wholesalers that have been doing this for 15 years and buy a deal from them.

A rider allowing for using your owner-occupied property as a short-term rental for a specific/limited amount of time is very different than an investment property being used as a short or long term rental 100% of the time.Also, telling your home insurance company that you STR your home occasionally does not give you extra coverage for those types of risks, it simply means if your renter burns your home down the insurance company isn't going to immediately deny your claim. 

The chart of accounts is structured around the Schedule E, so you simply export it and send to your tax professional.

On your own, you simply can not buy in the place where you want to live. 

You accused me of a lot of things here my man… a lot of things that simply not true.

Have proof on hand (easy enough to find) online of the missed tax payments and any documentation that supports that he specifically didn't pay his taxes.Probably a simply mistake on his part, but now if he wants to develop on it, he either has to land lease it from you or buy it back.I'm not sure how the whole tax deed thing works, so that would be something you have to figure out between the two of you.

They were referrals and the business started to grow simply because I had a competent team that was responsive and looked out for the owners' best interests.

If you want to know if it is a fair price for your area and this time of the year, simply get two or three more bids.

Another solution is to simply list it as an STR and say "contact host for long term rates".