I read their cc&r and the only thing I found that relates to rentals is a line that reads “Property shall be used for residential purposes only”But I’ve reached out to the hoa and was told “Our HOA regulations say single family home which means No vrbo or short term rentals.”I’m getting confused since I’m fairly certain that single family home doesn’t mean what they think it means.

But because I'm still relatively new to investment real estate, I was assuming I was missing something obvious that seasoned pros know that I don't.

Also, totally can relate with you being from an expensive real estate market - I moved to Columbus a few years ago (from Portland, Oregon which was super expensive) to become a full time real estate investor, and ever since, I've completed quite a lot of BRRRRs, flips, and own a successful rental portfolio here in Columbus Ohio.

We have property managers and don't run the small business, so my workload is minimal.Of course I keep an eye on the market, but finding anything for a guy like me would be way too much work. 

You may also want to call local property management companies to get their estimated rental amount and their feel for the rental appeal of your property in the area, etc.* Talk to your tax professional and find out what your tax implications are from inheriting the property to buying out your brother and putting it in an LLC, etc. * Also find out if the property's tax assessment changes with any of the scenarios above.

I think the actual settings will vary if you are managing directly on platform or using third party softwares, etc.As mentioned above I think risking going vacant over a major holiday will outweight the extra housekeeping cost.Also, I am not sure how much volume you are doing but do not pay cleaners extra for holidays. 

oh yea, I recently started my own business (2021 was my fist year in business, commercial door company, non real estate related venture) and gave up my w2 income and was already denied another refinance on my primary due to lack of self employment history. this was with the bank my business uses with and they want 2 years of self employment income on the books. end of 2022 will be 2 years so financing may be an issue if I want to 1031 now, but i havent really thought all of that out yet either. 

is the actual wellhead location relatively adjacent to your land, by chance?

A friend/relative that has either cash or equity that would lend it to for 6-8%?

With occupancy rates, utilities and bills the math works out that long term rentals are going to be more manageable.