https://www.biggerpockets.com/blog/short-term-rental-loans-a...High Level --Conventional will typically offer lowest rates/fees but harder to qualify, especially if you are scaling and past the first couple of properties or going for the high-end of the market-2nd Home (10% Down) - should be very careful here - these are not intended for STR properties and people using them for pure investment properties are entering dangerous territory (you are attesting to use it as a rental half the year or less, no management, need to live in proximity, etc.)- DSCR Loans - typically your best bet if you don't quality (or have "outgrown") conventional or looking to scale a portfolio or diving into more specialized markets. 

If I'm in your shoes (which I was a few years ago) I would recommend attending at least 1-2 real estate meetups a month to start putting yourself out there and networking with other players in your market. 

What general contractor recommendation have you used in the past that can pull a permit with the City of Chicago that you recommend?

This is 100% leveraging, which is high-risk, and it probably doesn't make sense because the loans will be more than the income.This property sounds like a good opportunity, but I recommend you find a way to save up for the down payment.

Also, searching the properties on the county tax auditor site shows that the property taxes on both properties haven't been paid since 2020 by the previous owner.

Austin has a few (check out @krisclarkk on IG) but I would go find a few of the bigger cabin or glamping sites to see who they used.

There are plenty of warnings about these big box "wholesalers" online.

I have a few properties in high traffic areas with at I plan to utilize by putting up some “we buy houses type signs”.

I highly recommend that you go to a weekend event with Scott Meyers and read several books on self storage.

@Stephen FrazierI'm not 100% sure what you're asking, but I would strongly recommend against buying something with 100% financing where part of that financing is a HELOCYou will probably just lose moneyIf the home is owned free and clear, maybe the kids would do seller financing?