I got a feeling that life as a Private-$ Investor may be a great place to start, and these properties lend a perfect means to testing that out, solving 2 issues in 1 action, because you can JV your way out of the operational side of things AND retain that long term financial upside. 

Multiple offers- On highly competitive properties, a concession can make your offer less attractive.

Recently, PM suddenly told me that this property needs "lead testing".My PM is not aware of this I already have 2-year lead certificate from the previous onwer AND assigned an inspector for lead inspection for me.

I am not a lender but I work with a lot of buyers who utilize second home loans and I am 99% sure you cannot buy multiple second home's in the same market. 

Would love to connect and maybe discuss strategies further.Hi Willis,Something that I didn't mention before and that could be unexpected is adding a separate entrance or converting a basement/garage into an ADU can appeal to landlords looking to rent to multiple tenants.

The LLC already owns the land and has for multiple years.

It sounds like you are mashing a lot of different things together here.It does not matter at all if you have an LLC, or if you, or your wife is the owner - it doesn't change any of the tax positioning in the slightest.The test to be a qualified Real Estate Professional is at least 750 hours in real property trades or businesses AND  over 50% of your professional time. 

Many will be well educated on their housing options guided by their brands, teams and universities, and are well capitalized and qualified on a short term 3-6-12 month basis, and I actually had a client purchase a newer townhome in Tallahassee for lease to a football player at FSU..Keep in mind the top earning NIL athletes stretch across multiple men's and woman's sports. 

No one was able to clear it, even after multiple attempts, and it caused Home365 to stopped paying my bills (pending owner contribution).

The 3 most important things for performance are pricing, multiple channels, and reviews.