STR is a strategy and an investment (furnishings, learning to self-manage, hiring cleaners, etc.)

They have a handy feature where you can manage multiple accounts for each of your properties but only need to remember one login.

I plan on hiring a general contractor ( like many do) and then hiring my property manager to manage him. 

It seems to be a very tightly managed building, which is typical for Ocean City, Maryland from what I have heard from my real estate agent and lender.

Since I will be leaving my corporate job and effectively self-employed as I manage most of my MF portfolio, can I roll my retirement savings into a Solo 401k and invest in RE with the money?

This guy is also capable of managing a lower skilled helper who will cost you $125 per day.

My PM company does manage some there though.  

It's saturated now and management fees are high for STR, up to 25 percent.

My plan is to self-manage the property and rent it out by the room, and I believe your expertise could provide invaluable insights to help me navigate this venture successfully.Specifically, I'm seeking advice on the following areas:Property Management Software: I'd appreciate recommendations for property management software that would streamline my operations and help me stay organized.Bookkeeping: Could you provide guidance on best practices for bookkeeping in rental property management?

If you've already done that or have a smaller budget like sub $30MM, I go to the best neighborhoods in the best cities, and buy the most distressed houses.I flip the one's in states where it's hard to manage tenants or re-fi into STR, re-fi out with 1-1.2 DSCR in areas where managing them is convenient in landlord friendly states.