What do you recommend?

Highly recommend you check into Jurny.

If you're looking for higher cash flowing markets, I recommend starting in Midwest because it's affordable and offers good cash flow.

Your strategy is possible but I would still recommend speaking with a CPA to ensure you understand depreciation recapture and intricacies of a 1031

Hi @Jay Lam, we always require all owners to sign the property management agreement, so I'd recommend going back to you PM and enabling you both to sign.Best of luck!

We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

We would like to do it all legally with plans approved by the town.Any recommendations for an architect / company that can assist us with this project? 

If not, I would recommend purchasing as it is worth it compared to a large investment you are about to make...

We try to do a walk-through with the new tenant at some point to show them emergency shut off locations, instructions on filter changes, etc. so I wouldn't recommend just dropping keys off and that's it, but I have had probably 2 or 3 tenants over the years that I never met, just talked to by e-mail or text.