You'll likely want to start with reviewing the requirements under Prop 19 for retention of the base assessed value when adding a child to title, and also look up the rules for a basis step-up at death. 

Here's a case study that would be dismissed based on your criterion:-Asset: Mix Use 11 Unit Building-Contract Price: $1.73M-Existing Rent Roll $15,800*Currently 1 vacant commercial space market rent $5,500 & 9 apartments all leased below market value (60 day termination provisions for each residential lease). -$650,000 Renovation Budget-Stabilized Rent Roll $25,400-"As Complete and Stabilized Value": $3.45MThat's a recent MLS deal in a B+ Philadelphia location with a credit tenant that's been there for 20 years in the occupied commercial space.

If you are going to do this type of business make sure it is in an area you can visit or make yourself familiar with, you have someone that is representing YOU at the table like your Attorrney, and you don't make decisions based on "we need to wrap this up". 

@Katie BustosWhen you buy a home with a rental unit, like a garage apartment, how you're taxed can change based on how you use the property and if you rent to family or others.

The question I have is when Customizing your estimate on expenses in AirDNA.

Often it is based on how well you pay back history.

I have customers that own restaurants , and they own some pretty sweet houses . 

even with higher rents once you calculate in the taxes, insurance and PITI based on the price its little to No cash flow.

Based on my research it seems like with a little rehab and managing a short term rental effectively, short term would likely cash flow more in a market like Tampa. 

I understand there are risks to this too, but putting an offer, with the caveat of based upon complete financial review, might be more enticing for owners on the fence.