He also does solar deals that are out of this world in Hawaii but you need to be a Hawaii resident to get the full benefit.. what size are those developments?  

In addition I am giving him freedom to explore (to a certain extent) on my dime.

When you move forward, they should provide proof and name you additional insured.

You will need an additional $300-500/month budget for capex.

Use extended closing periods or additional earnest to buy more time for your old property to sell if you need.The last option is what's called a reverse exchange.

I have been trying to keep an open mind while I learn about the different strategies but I see a lot of benefit in the multi family and SFH units for long-term rentals

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. 

I'm just here to note that an LLC does not offer a single tax benefit, nor does it allow any deductions that aren't allowed without an LLC. 

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

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