I'll keep you in mind if I device to pull the trigger.

I guess it triggers the "sunken cost fallacy" part of their brain.

Dig into reverse mortgages before pulling the trigger on anything, specifically HECM's (FHA product).

Airbnb has this judge injury thing were they can rip your booking out from under you when the guest claimed extenuating circumstances. another nice thing is I haven't really been asked to review and I haven't really received reviews on booking.com like the insane hyper-focus on Airbnb.

Rental Income Consideration: If the property generated rental income while it was debt-financed, the portion attributable to the debt could have triggered UDFI.

However, I notice that Personal Injury is not included and I'm thinking that may be important to have for a Short Term Rental.

looking to pull the trigger soon. 

But the answer for everyone may differ.Here are the personal attributes I see in those able to achieve a higher than market ROI, enough higher to be able to “scale”.1- Knowledge of real estate principles, real estate law and real estate finance2- Minimum 3 -5 years full time, or near full time experience directly related to real estate investing3- Ability to utilize technology for increased efficiency, capacity, and accuracy4- Excellent hired legal counsel and excellent hired marketing help5- Established method(s) of obtaining consistently high QUALITY deal flow6- Ability to manage and choose people who are NOT employees: Attorneys, Appraisers, Mortgage Brokers, Real Estate Brokers, Title Companies, Surveyors, Marketing Specialists, Accountants, Contractors, Consultants, Property Managers7- A VERIFIABLE track record of success8- Ability to identify, analyze, and negotiate a deal that can be “worked” for “enhanced” ROI9- Some type of competitive advantage; for example for me it’s my ability to analyze and identify mortgage loans that are actually less risky than all other lenders believe (on the investing in debt side), and on the real property side it’s my ability to analyze”pull the trigger” with LESS information than other investors need,  combined with the ability to pay cash, or raise significant capital almost instantly as well as being able to obtain loans at the lowest prime customer bank rate with no recourse or personal liability.  

Your best bet is to get on the phone, get multiple opinions, multiple quotes, and make decisions on the type of build before pulling the trigger.

Converting a traditional IRA to a Roth triggers taxes on the converted amount, so plan accordingly.