Could you pl explain a bit what are the flaws in my approach.

Currently, I'm analyzing different markets to see which one will best match my strategy.

Convention lenders said they are OK with this approach, but in PA not sure paying the transfer tax twice (once at sale and once at transfer into LLC) is worth the savings on the interest rate between the conventional vs DSCR (just pay transfer tax once at sale).

We know many agents in our market that are really clueless beyond the basics of tenant screening. - You have no recourse against an agent or PMC once you pay them for the placement and it turns out to be a terrible tenant:(If you have the time and network and post here for assistance, it's always a good idea to learn the rental business from the "ground up".Of course, one mistake can also cost you thousands of dollars.

Based on my experience managing a significant number of rentals, leasing back to a seller can work, but it’s essential to approach it carefully.Lease Start Date:The lease should be signed at closing and start on the same day—Monday in your case.

You'll probably get better service approaching it that way than hiring a professional manager anyway.  

Experienced managers can help evaluate potential investments by providing insights on rental demand, market rents, tenant preferences, and location-specific factors that affect leasing success.For example, rental properties need to be close to conveniences like major roads, shopping, and schools.

If either of these homes has been your primwry for anywhere approaching a year.

All indications here are of a pretty healthy market. 

Granted, the real estate investing market was better in 2016 than it is now.Best of luck to you with whatever decision you make.