I know there is a lot of hard work involved and I am up for the challenge!

It does not seem like you have a good handle on what you would want to do there so It would probably be best to rent it out. 

Is there a lawyer or a Title company that must handle this transaction?

It is challenging to find a property at 75% - repairs - wholesale fee to assign or close on.

No need to expand on why etc that just opens up more opportunity to challenge the reason.Same thing here, she's disqualifying the tenant based on their failure to  transfer utilities into their names.

I manage it remotely and have two trusted people that handle maintenance/repairs/tenant issues etc. 

Challenges?

(You can rent two rooms to the same party but can't rent each room to separate parties.)The process for handling violations has been revised to a tiered system, so you're not automatically going to a hearing because a nosy neighbor complainedMaintain $500,000 of liability coverage.Can't use the STR for large gatherings like weddings or commercial events

I've found someone that I trust to handle this, so have concluded that nothing can go wrong and it will all be smooth sailing from here.

Challenges?