But we have a smaller one (1100 sq ft) in a lesser subdivision and not gatlinburg  that is getting tons of activity since we put it up for sale and it isn't complete. 

I'm in the camp (tax-wise) that there should be a Flat tax or better yet, National Sales tax with no deductions for anybody or anything......so obviously the concept of depreciation would go away also.

So if you can collect rents into your business either by deeding the properties to your LLC (be careful of the due on sale clause on your mortgages) or by signing a master lease between you and your LLC and having the LLC sublet then that may help.

Would this cause any tax implication towards a future sale  of the home purchase?

FSBO (for sale by owner) sellers get sued more than any other group in real estate.

I started investing in 2019, got my license in 2021 and was initially with a residential broker that was primarily focused on retail transactions (aka sales, purchases, leases, for regular end user folks). 

This could help with sales and capital gains tax."

Do you have a nice amount saved up for the activities you enjoy(I assume yes given a 30+ year in Tech plus you mentioning making lots of money already in real estate).If that is the case, what are you looking to achieve now within real estate?

I was hoping to get some shared insights into what the best starter tech stack looks like for a wholesaling operation.

This will primarily effect tenant's sales and your ability to re-lease when tenant moves out.You have building risk: primarily, how easy will it be to re-tenant if your tenant goes dark or leaves.