Start communication about 2 months prior to the lease ending sending out renewal emails and following up with a text or a phone call to confirm.

I've been super happy with it.Regarding a bookkeeping software, bookkeeping for REI companies (especially rental property companies) is super nuanced.

I would confirm the other four owners and would not buy there is they were all the same family, it will just be miserable most likely trying to deal with 4 against 1 (unless they all hate each other).Your second concern is valid and correct.

or software to use?   

An arborist would be who I would ask, this is a tough guess for anyone not there to confirm these can be moved with no issues.   

. - What systems/software do you recommend to use to determine the markets to invest/buy into?

Have you confirmed all of the possible use cases and what you would need to do for multifamily vs. mixed-use?

We add the tenant to our management software to streamline communication throughout the lease duration.

I would recommend you really take your time selecting the right software.

I think I would only move 3 of them to software management at first, see how that goes.