Ideally this is research you perform as part of your underwriting when deciding to build the JADU.  

If this isn’t the first step to building your real estate empire, sell and don’t look back.Owning a property which is netting -200/mo in quality location in a quality city isn’t terrible, but not ideal either.In your negative 200/mo are you accounting for pm fees, maintenance, capex and vacancy expenses?

Banking on appreciation to pay back your investor is not ideal unless there is an immediate value add play for the property.

I deal with this issue all the time.

It's ideal to know these in advance before pursing the property. 

to give some feedback, you will need to estimate the cost to repair the house; if you don't know how to do that, we just need some  information of what the house needs and the sqft of the propertyIf the house is, as an example, 2500 sqft, and It looks like you are stuck in time back in the 1980s, but the AC is working,  the roof is ok, and there are no foundation, plumbing, or electrical issues; I can assume maybe a $20 per sqft, so the rehab is about $50K to 60KIf the ARV is 290K minus 10% closing/holding costs, - minus 20% profit - $50K rehab, ideally, in this example, I need to buy the house for about $150K to flip it, but as a landlord, I may be able to pay a bit more, as long as rehab is not too much, and rental is about $3,000 to $3,500 a month

Ideally, we would just like the tenant to move out, regardless of the new rent or not.We have changed our mailing address to the property and have the utilities in our name, but are currently living with our in-laws while we renovate the first floor.

But would still prefer driving distance, so CA and South of Pismo beach ideally. 

I'm assuming you'd want to use this benefit for a new construction to get exactly what you want built, since finding this type of property already built & ready for sale isn't ideal, not impossible, but not ideal.

I am really trying my hardest to purchase at least 1 other property this year, ideally 2 more.I am looking for slightly distressed properties in the 50-120K price range (yes it's possible), should I look into borrowing money against the condo?