Determine how comfortable you are with potentially locking up assets for a long time and how much risk you can tolerate.Market Conditions: The situation of the real estate market might change, and this could have an impact on your choice.

Are there any situations under which you would  buy a property with a negative cashflow? 

The House Hacking Strategy: How to Use Your Home to Achieve Financial Freedom" by Craig Curelop: Written by a real estate investor who achieved financial freedom through house hacking, this book offers practical advice, real-life examples, and actionable tips for aspiring house hackers.These books provide a wealth of knowledge and practical advice for anyone interested in house hacking or real estate investing in general.

As you're preparing to search for a rental property, my advice would be to lock in your financials so when a great deal comes your way you're ready to strike! 

I am a lender here in South Florida and would be happy to provide you with some more guidance so that you can make an informed decision on comparing conventional versus FHA to see which works best for your situation. 

Your financial advisor has the historical information from every DST sponsor.

Aloha George, we work with a lot of elderly homeowners who are in reverse mortgages or in distressed situations. 

Do you think a self management software can work in my situation ?

I am considering using a different strategy but will STR again if I can't financially figure out how to make other strategies work.

I've never really heard of a better "win-win" situation than that.