As a landlord you might want to go with a cheaper "named perils" policy instead of a comprehensive homeowner policy.I guess the good news about your HOA fees is that you're not being hit with an assessment in addition to higher fees. 

Additionally, in the past six months, I’ve reviewed about 45 multifamily properties (ranging from 10 to 80 units) for my real estate private equity firm.

You pay your agent at closing (think of it as an additional closing cost) Depending of the situation and of these options can be used by you and your agent to negotiate with the seller.

Best Value adds are:Updated kitchen, updated bathrooms, cosmetic remodels.Additional bathrooms - finished basement spaces, in unit washer dryer, central air, additions/alterations.All of those are useless though if your roof is 30 years old, your mechanicals are from pre 1950's, and your home is in dire need to be renovated "behind the walls"Otherwise the above will increase your value but you will be left with Lipstick on a Pig

My lot is over 13,000 sqft and I have the space to build an additional unit.

Homeowner should have an adequate policy and you can use additional damage protection from services like Safely and Waivo.Yes, security deposits are normal for MTRs and highly recommended. 

I would keep the work very cosmetic, and I would enjoy the additional space and/or revenue from the unit without considering digging up, etc. 

Pace also has shared his legal documents with the community which get updated.When I joined this lifetime membership I didn't realize how much additional value he was going to share.

Meeting some people tonight there to create a scope of work and do some additional discovery.

In addition to what was said above, for the software that has a free trial option, sign up for it and use the software for a day (or at least a few hours) as if you are using it for real, then call their customer support too and get a feel for that.