He makes the owner an offer where HMH Wholesale takes over their position in the loan (Subject to deal) and the owner walks with $10k (or so) cash.

That’s easier for a buyer to get into the deal, but for the seller it translates into them getting $38,400 for that same land instead of only $25k.The seller could also do a land contract, with essentially the same type of terms as with the owner-financed deal, the difference really being that instead of the seller having just a mortgage lien on the property till it’s paid off, they actually retain full ownership of the land until the contract is paid in full.I would have the seller tell you what they wanna get for it, then tell them you’ll add your fee to it and find a way to make it happen… and then come back a day or two later and tell them that you found a way for them to get their price, for you to get your fee, and for it to still be appealing to potential buyers… Then walk them through the deal, how it’ll work, explain to them how your way is more beneficial for them overall, explain how your way opens up the floodgates of potential buyers now, and most importantly explain to them that doing things deals this way is very common when buying and selling land, and how its really the only way for them to get what they want outta that land 👌If you act like an expert on the subject (or at least more knowledgeable than they are) I promise they’ll most likely just follow your lead because they trust you to get it done.And if they are truly motivated to sell, then they’ll welcome with open arms any creative thinking that will help them get what they want.Good luck!

I've posted in this forum before on this subject (Chicago Mid-Term Rentals). 

HI @Jyotin GautamShort answer is no in Texas Long answer according to the Texas Real Estate Commission " Under the amended rule, a broker could give an unlicensed person a gift of merchandise having a value of no more than $50 and this would not subject the unlicensed recipient to a charge of unauthorized practice as a broker, nor result in a violation of TREC rules by the broker giving the nominal gift."

With respect to your 2 questions, 1) when you sell the property, all the depreciation taken (regardless of whether it was used to offset income in the past) is subject to recapture.2) You can reduce your taxable capital gain by subtracting the selling expenses from the sale price.

@Chris Seveney, but you forgot to mention that the email subject had 3 fire emojis, 3 dollar sign emojis and some arrows to make sure you see it.This reminds me of a the language the Mogul Club uses.  

Any insight on this subject would be greatly appreciated.

Typically, any additional income outside of salary is considered.Sometimes if C-corporations or S-corporations hold your rental properties, the court may even decide that the retained earnings are subject to child support calculations.

I've been trying to find a definitive ruling on the subject for MD, but it seems there are just general usury guidelines that a landlord SHOULD follow.

It’s “illegal” to purchase a property without the approval of the existing note holder (subject to)2.