When it's time to renew their lease, ask them what small upgrade you could make to their home to increase their quality of living.

Not in too bad of condition but definitely can be spruced up.What would you improve in this rental to add value and  increase rent just from looking at the photos?

I will probably work on private money sooner than later too, just don't have enough confidence in the whole process on this first deal.

If your deal needs rehab work and the value will be increased substantially then a short term loan would be ideal. 

The occupancy rates will increase some as some people book last minute but using occupancy at near start of month has some safety margin built in.What this snapshot does not make clear is whether there is significant variation by month.

I was held up a month for a plumbing inspection so plan to increase your hold times as it will take longer.Are you buying the property from a builder or owner?  

What I'm really looking for is someone to JV with on a few wholesale deals to help get my confidence up and get things rolling. 

I'm speaking as a beginner but couldn't feel more confident in the approach of building initial wealth through frugality.

( Suppose the cash flow is $400, it means it would take me $15000/$400 = approx 3 years to get back my $15k) That would mean hoping the price of the property increases because of the flooring.

Just between the increased Vacancy amount and insurance I believe it will wipe out your Cash Flow projection.You will find it in your best interest to stay conservative with your numbers.