If he is broke, its just a waste of your time, and I would say cut your losses now and consider it a lesson learned.

So in my mind STR is good tool to catch long term appreciation and REDUCE EXPENSE when folk is vacationing.For me it is as the following:if you like snowboarding you would buy in Tahoe or Denver or Aspen.if you like beach you buy in Hawaii, Destin, Panama Beach FL or San Diego.if you like hiking/forest you go to these Servier county,etc.The problem is if you don't have hobby and don't like to go for vacation LOLI cut 90% of my vacation budget by having STR, this is the internal profitability metrics LOLIf my own purpose is to make money I would find investment that yield 30% IRR and >1.5EM and I know it's not that in vacation market in 2023 lol.

You need a differentiator, an edge.

I had more than one appraiser comment that the CLV market is a declining market in their reports and when lenders see that they often cut leverage.A lender will ask for your credit, experience, and maybe liquidity. 

My feeling is that the tax evasion thing cuts both ways. 

The only issue I can see by initially circumventing your agent could potentially be "cut out" of the deal and/or their commission when you do end up writing an offer because the listing agent could argue that your agent was not "procuring cause" for your interest in the property since you contacted the listing agent directly and began negotiations. 

I’m much more into this than she is lol she’s not against it just doesn’t push for it like I do, in addition to the fact we will cut our possible mortgages in half if we both go on the same one)My realtor is pushing for us/me to look at more expensive multi’s as there’s less competition and potentially bigger returns.

I am wondering are people competing against your rental with for sale units, meaning you might have to price cut the per month rather than give just a two month discount.

I currenntly have 5 properties and am needing to cut down on tax liabilities for this year.

Getting a good PM would also go with your wanting to do less, but it will cut into your cash flow.