I think most real estate agents won't waste time on buyers who are "coming in with an offer well below asking" with their main justification being they want to pay less, fishing for that rare seller who will randomly accept a much lower offer before dropping list price first to generate competition. 

They rarely foreclose on a IRS lien.

With the lower LTVs offered by senior lenders these days, it may be tempting to look at preferred equity and it may make sense since technically it is cheaper than LP equity, but also keep in mind they have a higher liquidation preference (obviously) but will often want all the cashflow (or a majority of it) to come to them before the LP investors and will also want large reserves, so make sure you model out the cashflows and understand the end-to-end deal with the preferred equity investors.We have some institutional investors with whom we did a combination of a pref and JV deal and it worked quite well for everyone including them and the LP investors.

Quote from @Michael Lynch: People rarely talk about the amount of effort involved in operating a STR.Never sell a property unless you have a clear plan to reinvest the money into something that will perform better or move you closer to your goals.

If he has tons of time on his hands and wants to get his hands dirty, flipping could be an option as well, with a combination of his money + private money. 

A combination of mortgage notes for cash flow and desirable properties in high appreciation areas (not cheap, undesirable properties in the Midwest.)

I have seen some sellers wait two years to close on a property those are definitely rare circumstances.

Getting a building permit is rarely a cut and dry process.

I would recommend a combination of a house-hack and an investment property depending on your current cash position, short-term and long-term goals. 

@Piper WatsonPay down the credit cards as the chances of earning a return that is at a greater interest than the credit cards is very rare and risky.