Additionally, I estimate the value of their holding to be $250,000 in addition to the $125,000 they put in upfront. 

Ultimately our main goal build a portfolio of multiple different types of investment properties, buy and holds, rental properties, and fix/flips; but the wholesaling side of real estate seems like an attractive venture as we are just starting with little capital and it could provide us with a revenue stream to become a cash buyer. 

@Kelly Schoeppler my approach is to add the subletting tenant as an "additional occupant" and continue to collect rent from your current tenant.

While its significance may sometimes be overlooked, generative AI holds the potential to revolutionize every facet of the real estate lifecycle, from transactions to property management.Decoding Generative AIAt its core, generative AI harnesses the power of data to generate fresh content or forecast potential outcomes.

You can ask at your county to see if they or anyone else around teaches the basics.I've been to several of the free pitches of the national touring acts...and most gave enough wrong info that it wouldn't make sense for most people to take the class or pay additional money over the free pitch to get started.   

The party with custody of the funds has the legal obligation to do this under the tax law if they hold the sales proceeds.

How does this work, and is there an advantage to this strategy for a buy and hold investor? 

Definitely open to connect.....even though I'm a Boilermaker.......won't hold that against you!

You mention multiple states in your title, such as Indiana and Illinois.When choosing a professional, make sure they understand multi-state taxation in addition to real estate taxation.

Buy and Hold?