I wonder if by putting my back against the wall, can I make more money using this cashout than working 9 to 5 everyday.

My preference is to go straight through the title company, put that money into renovations, and send the agent a couple hundred dollar gift card to Amazon for their time. 

When you do that you put too much money into a Non ROI type of investment.

If you notice my posting history I am investigating purchasing my first condo in the next few months and am investigating some potential scenarios.I am looking into living in the unit for a little over 1 year and putting it up for rent either with HCV/Section 8 or finding a tenant through my brokerage(L&F) or other means. 

And if I was one of your clients, I would much rather you put your energy into defending me in court, then learning how to properly patch, sand, tape, and prep the walls for painting.I personally have painted a couple of my own projects, but I had the time and somewhat knowledge and experience, and also had run to the bottom of my budget at those times.A few tips/comments which may be helpful:*  As someone else previously posted - gets multiple quotes (3-5)* Ask you fellow realtor friends/associates for painter referrals* Check NextDoor.com for painter referrals* Go to the professional paint stores (Dunn-Edwards, Benjamin Moore, etc) and ask them for referrals.

It sounds like you've put some capex into these already.

Where the tenant puts his info out there and what he's looking for, # of pets, what he can afford,  etc. 

Best options would be either 1-Buy a cheaper older home or 2- put a down payment so that the mortgages is more feasible to rent out.

We put together $29.7k to bid at an auction and won a single family home for $252k leaving a balance of $222.3k.

Id really try to make staying put work.