I will bet they will be have a big issue in their underwriting.  

Having everything together will be your best bet..

I would bet money that Analysis Paralysis/ never starting has ruined far more real estate investor careers than bad deals ever have.

Because with judgment liens lasting 20+ years and federal court collection powers, you better not miss.Question: Is your estate plan accounting for potential judgment liens, or are you betting the IRS won't be proactive in the final months before CSED expiration?

The key thing is your trustworthy person - cleaner, handyman who regularly checks and lets you know which supply is needed.

@Ethan Rolnick-the best way to start is with a house hack, period-real estate investing does require money - any methods purporting to not are high risk-your best bet is to save up for a house hack. 

High fee 8% / 10%, they are the most reliable companies in most cases, sometimes the leasing model is to hire local agents that gives a better marketing on your property to reduce vacancy rate, and when offering betted vendors they have the best prices.2.

I think we're in a buyer's market here in Austin for the next 1-2 years at least if you were to ask me to make a bet on it.

Would QuickBooks be my best bet or is there something else that would fit my needs better?  

I don’t care if they don’t like my offer, they can say no, I bet they haven’t lost 60k before, it hurts.2) don’t over rehab: contractors and materials cost lots these days3) buy light cosmetic rehabs.