It's pointless and only causes issues.

We actually have the option to STR on a few of our properties and decline to do so because we make more money than an LTR on our medium-term rental with a lot less work than an STR.The pros to medium-term rentals: high occupancy rate, no local regulation issues if you are 30+ days, elevated rents, more and more people are staying longer, often the midterm rental tenant pool is professional. 

I think this makes everything cleaner for taxes, documenting historic rental payments, and legal issues that may arise due to the barter, etc.  

The major issue is that the some windows are moldy and some have rotted frames.

Is he required to issue me a 1099 form for rental income for 2023 taxes?

Giovanni, I do it very similar to Scott, although all mine are posted as cash offers, although I have a very close relationship with my HML, and he always takes care of my proof of funds, and I honestly have never had an issue with this or ever been questioned, and I have done purchases from all sorts of sources including Fannie.

It just becomes a marketing and pricing issue. 

Ours was an occasional rain issue in one corner and also a bit of an uneven floor. 

With some of the CapEx issues/concerns that came up during the inspection/prep work for construction, we delayed some of the work when we should have just addressed them all ahead of time.

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