However, based on our conversation, this strategy might unnecessarily complicate things.As a 1099 contractor, can I deduct all upfront expenses for the STR upgrade, as I did with my San Diego property?

If they ask why, I've always said so both our credit isn't burdened unnecessarily. 

www.costar.com/article/249461865/jury-finds-brokers-conspire...A jury in Kansas City awarded almost $1.8 billion in reimbursements to Missouri home sellers who accused the National Association of Realtors and some residential real estate brokerages of unnecessarily driving up the cost of home sales because of their long-running practice of buyer and seller agents splitting commissions.The more than $1.78 billion awarded by the jury will be trebled, or effectively tripled, so the damages total almost $5.4 billion, pending appeals.

Adding layers of business could complicate things unnecessarily; items such as taxes and legal fees may increase greatly etc.These other factors would greatly play into what my next move would be.

.- i'd encourage you to consider doing as big a deal you comfortably can with the amount of capital you have, vs trying to start off unnecessarily small. make sure you account for a personal reserve, a reserve for the future property, and closing costs, THEN see what's left over for a down payment. also note that while there are creative ways to buy tons of RE with little $, they demand A LOT of time and energy, which it sounds like you guys may not be looking to invest right now. - driving distance vs long distance: try to map out exactly what situations this would benefit you in. could either of you guys logistically drop everything to drive multiple hours away?

-not sure who said that, but you're far more likely to make a dumb or unnecessarily risky decision right after you hit a home run on a deal.

Cooking" meth can produce considerable contamination, yes.Consuming meth can take different forms from simple ingestion which leaves no residues  to smoking which will will leave residues. 

Account Closed- Your information affirms why I think we are taking a bath on this deal unnecessarily.

@Tom Smith Although I agree, REI is a great suggestion for the potential returns and tax benefits, the hidden fees you mention aren't necessarily a 401k problem, but the a downside of certain 401k administrators and custodians that unnecessarily limit participants in their plans.

Just make sure whatever decision you make, that you do not do anything that unnecessarily sends red flags up to the IRS!