That depends on what cash you have on hand, the prices in the area you are buying, the rent to price ratio, and how well you landlord.

Also, build relationships with local suppliers to negotiate bulk rates, and stay hands-on during rehabs to gain valuable experience.

Depending on the extent of the rehab on property 2 it would make sense to have that completed by a contractor before handing it over to the new PM.

Loan programs that utilize AirDNA income projections to qualify can also be utilized for cash out refinances (if not currently operated as an AirBNB) although some lenders have a maximum cash in hand of $500k-$1M typically at a lower loan to Value of 65-75% for investment property vacation rentals. 

Many landlords on this forum miss this - they often tend to be conservative in their political values - conservative policies, in that sense that they are "landlord friendly" also tend to go hand in hand with policies that make adding new supply easy.

However, it has shown me that that type of contracting is not my passion and I want to really take my life into my own hands.

I have about $180k in equity in one of my investment properties and I have a nice amount of cash on hand and I have an idea that I would like your thoughts on.  

but you are right in not handing over any money until they are out and you have the keys.

Hi Joseph, I own 3 SFR long term investment properties, and have gutted 2 down to the studs and rehabbed.Then I help out a handful of investors in various ways.

I wouldn't say it's a red flag but I would ask how much reserves the property currently has on hand.