I am shoppping the property to potential buyers.

Plus, the potential tenant will appreciate and pay more for a new home rather than an older home.

I want to place wifi water sensors in all the major potential leak areas around the house.

This document summarizes the primary goals of investment, discusses tax benefits, and examines the potential returns and hazards.

It's pretty straight forward to analyze the potential if other STRs are nearby.Did into your Airdna.co data and see how the best performers are doing.Let me know if you need help.Best to you

Before the Karens potentially in this thread get self righteous I am not providing legal advice and @Adam M should retain proper legal counsel to prepare all documents associated with this syndication including compliance with SEC regs. 

The first property was a long term investment but I have a lot more flexibility now and am strongly considering moving there to house hack and potentially start building a portfolio.

I wanted to create a checklist of potential major problems to look out for when considering older properties (pre-1960 build), especially regarding deferred capital expenditures. 

I think a more prudent (and achievable goal, not to mention far less financially risky) would be to start free classes/seminars to teach them how to delay gratification, increase their education and earnings potential, find quality and affordable child care (perhaps creating a "swap group" within your group for free trade-off CC), learn how to properly manage finances, and all of the other tools needed before you can even begin to invest in real estate.

Me and my team would certainly be open to a quick consult to talk through your goals further and help unpack some potential additional approaches you may not have considered.Congrats on the recent acquisition!