I’m currently looking into the best ways to structure guest payment flows to ensure legal compliance (that may restrict non-licensed property managers from collecting rent directly) and seamless operations.

The worst part is that it's usually way too easy to get your license, and the consequences for these sleazy agents are usually non-existent or not harsh enough. 

There are significantly less opportunities for HELOC on non-owner occupied but there are some (you would likely need to investigate to find a few).  

I have a 1/1 and a 2/1 and although I'm seeing lots of different types of travelers, the ones who have been booking my place have all been traveling medical professionals.

Non-conforming/portfolio loans, which aren’t conventional loans, will allow as little as 20% down. 

The seller’s most recent counter-offer was 90k for 30-40 day closing with a 10k non-refundable earnest money deposit.

Indeed, the FAIR ordinance is anything but fair to non-corporate landlords, seemingly punished for investing in rental houses to generate income as an alternative to stocks and bonds.A handful of opportunists likely could learn to exploit these new rules, preying on otherwise law-abiding landlords to obtain legalized shake-down payments.

Lots of fakes out there so be careful.And its not so  much they will steal up front money from you.. but you waste time and money finding a place thinking they are going to fund you put up non refundable EM spend money on inspections only to have your deal die because you got with someone who cant fund or never could fund. 

Take a look a look at the RPAWi. org, which is our local non-profit landlord association located in Milwaukee.

I have purchased apts. in foreclosure because the lender did not know that they had negotiated a non-recourse loan with the owner.