But my lack of long term market understanding lead to over extension on my personal buy-and-hold properties. 2008 destroyed me as 95% of my tenants decided they no longer needed to pay... and some even decided that they were entitled to my mechanical systems and metal materials like plumbing and wiring... one even burned down a multi-family building.

Every one of my projects has been extensive remodels.

Make sure you do extensive Due Diligence but don't get "Paralysis Analysis", the over analyzing of something which causes enough fear to  stop you from taking action and making a move.  

I offered her a one month extension til October 31st.

@Alex Sanfilippo This publication should be a good (and extensive) resource for you. https://www.irs.gov/pub/irs-pdf/p587.pdf

While finalizing my extensive rehab plan (removing walls for an open concept, expanding a shower in the master bath) my contractor mentions we need to have an architect draw up our plans in CAD and then we need to have an engineer bless the plans in order to get through the City of Houston'a permit process.

Since you are new to investing I wouldn't get into a full blown project requiring extensive repairs.

REO or HUD transactions ad another level of complexity and require their own paperwork, which is extra extensive and hard to understand if you lack the background. 

That way, you develop a more extensive list of all types of Buyers/Investors as well as find more Properties and their freshly-convinced Sellers in every niche - by giving those Sellers MULTIPLE options!

I've seen posts on craigslist similar to car wraps but not quite as extensive but they were looking for people willing to have an advertisement put on the back window of their car stating something along the lines of "We Buy Houses" with a few bullet points and a number.