But I find from personal experience and from my buyers' Airbnb experience that it's a bit of a hassle trying to get guests to rebook at the new listing.I don't know how strict Joshue Tree is at enforcement, but in Denver and Colorado Springs here, you could probably get away with an STR listing for three months without the license.

So, here’s my question.. do you think you’d be more comfortable taking the DIY approach with strict guidelines, or might a property manager give you the peace of mind you need?

I do have several S8 rentals, while they are generally performing well, there is more paperwork involved in the leasing and the strict inspections can be quite a pain. 

Consultants, inspectors, and mentorsProperty managersAssistantsBookkeepers, accountants, and attorneysLandlords if you rent your office spaceYour business partners if you paid them (except if they were strictly lenders)Disclaimer about wholesalers: it is a controversial issue, with some of my colleagues claiming that wholesalers do not need 1099s.

One key takeaway from this deal was the importance of sticking to a strict renovation budget to maximize returns.

However, the process can be complex, with strict timelines (e.g., identifying a replacement property within 45 days and closing within 180 days).

Ive been using the same for many years now and its my foundation for operations, follow-up, workflow management and communications. 

Follow Teresa's advice.

Does the lease also state that the tenant must follow the HOA rules? 

We have purchased 8 investment properties over the last 2 years, we strictly rent them out with section 8.