However, beyond that if they are honest in assessing themselves, they might choose to hire or partner with people who can fill the other roles needed such as a realtor, accountant, lawyer, etc.

Since you own a business, you know the importance of being hands-on, but short-term rentals will require a mix of sweat equity and automation, especially for guest turnover and property management (as an investor/broker I've worked with a lot of clients that have done STR, and are now pivoting to MTR). 

You're absolutely right—the location plays a significant role in determining the best style for a fence.

Ned Lamont emphasized the role of homeownership in building wealth and community ties, with the average loan amount at $30,000 per household.Despite the program’s popularity, Sen.

If you trust your contractor and can stay on top of the project, you might not need a property manager my understanding is the property manager is playing the contractor's role for some smaller projects, not another layer on top of the contractor. 

Then pivoted some units to MTR.

His criminal record shouldn't play a role if he was released from prison five years ago and has held a steady job, has good landlord references, etc.Disorderly conduct looks pretty minor, and I don't see how it poses a risk to you.

Just may require a pivot from vacationers to the above type customers to get your numbers looking better.Hope that helps.Mike

It sounds like you're in a pivotal moment with a lot of moving parts—seller financing coming due, repairs needed, siblings renting from you, and a move to a new state.

Do you think the high property taxes play a significant role in shaping your investment strategy moving forward?