I plan to get wi-fi in each building.  

Each has its own advantages and challenges, and success depends more on the specific property, location, and your management approach.The "forever apartment" concept rarely exists.

If you don't have a plan for all the money on a cash-out, then you may be better off taking less and holding onto your equity.

I would want some major security deposit on file - maybe 6 months rent (personally), and / or possibly have them carry an insurance policy with you as the named insured for a descent value for any damages, etc - with the policy specifically written for the type of business they are actually running.

I plan on talking to my realtor soon, but I figured I would try here first.

By strategic, I'm assuming you mean brand/positioning/strategy and not specifically social media marketing, correct?

Techvestor's project managers direct local contractors to make the STR-specific improvements they desire.

Does this sound like a decent plan?

We plan to add a bedroom and a full bath to the basement.

Working with a reputable lender and having a solid plan for each project can significantly reduce risks.If you decide to use hard money lending, it’s important to calculate your costs and potential returns carefully and ensure that the projects you undertake align with your financial goals and risk tolerance.