Since I have to choose one type of platform/system and find alternate solutions for the features from the other side, I choose a STR platform because the LTR features are easier for me to recreate or do manually.Specifically we are using Hostfully as our PMP and a few other apps to supplement.

If so, find the best passive return possible and create some supplemental income. 

If you need additional income to supplement and have less net worth, cash flow properties for cheap might work the best but for someone who does not need additional income gambling with appreciation might turn out beneficial.

No one wants to put 70% down, so that forces the buyer to get a supplemental loan at current market rates, “plus some” because it is a second lien.  

Additionally, she is used to the lifestyle that my dad used to provide while he was still working and she currently spends about $6000-8000/mo (a lot of which is also medical expenses for chronic conditions), so she withdraws from the stock portfolios to supplement current spending.

Property is in Escondido, CA.I have purchased directly from the owner twice prior without getting a supplemental increase to the accessed value for property tax purposes. 

Do you advertise on either air BNB or VRBO.com as a supplement to your website? 

You may need to supplement the building policy in some ways.You'll also need liability coverage and, if you're occupying the condo, coverage for your personal property.

How about supplementing the the question with "in this post Dodd-Frank era?"

Then actually do everything they tell you to do.There are a lot of ways to supplement your income while you pursue real estate full time, if that was something you wanted to do.Hope this helps!