Quote from @Michael Baum: Hey @David Rutledge, the purchase of a small hotel is a very different animal than SFHs for STRs.Like @Luke Carl said, you will have to have some significant skin in the game.

I'm new to the game but I have been prospecting for deals for a while now.

House hacking in Chicago can be a game-changer—letting you live for free (or close to it) while building wealth through real estate.

Additionally, while rates aren't historically bad right now, they are higher than 4-5 years ago, and they will be even higher for you as an investor than they were as an owner occupant, which is what you were when you bought originally.I get that you are anxious to add to your portfolio, but that could be achieved without touching your first golden goose.Sometimes on BP, the push is to leverage every last spare penny, but that can be a risky game as the markets shift. 

(Please don’t tell me you will lend anonymously to those you met here or on the web).Title/Fire/Hazard Insurance Requirements: Not part of this list but what will be your insurance requirements?

There are several articles that do an exceptional job of explaining who, what, where, why and how tax payers qualify for the ‘STR Loophole’ listed here:The Short Term Rental Tax Loop Hole: A Game Changer for W-2 Wage EarnersThe Short Term Tax Rental Loop Hole: What Investors need to know The implications on the Oregon and California Coastal STR market is a strengthening buyer pool for luxury rentals in the $750-1.5M+ range.

I understand it isn't easy, especially when new in the investing game.  

He didn’t just answer my questions—he showed me how this game is played at a much higher level.

Just keep in mind the process can take a little longer since you’d need to work with contractors and follow FHA’s requirements.4.Your End Game: Whether you’re planning to stay long-term, rent it out, or sell once the work is done, it’s important to have your exit strategy mapped out.

2) Many flat fee PMC's charge whether property vacant or occupied, tenant paying or not.Lots of games also played with Maintenance fees.