So there's two  question I have with this scenario:1) Since I'm max out on my employer 401K contribution, can I still make contribution in the amount of $1000 after tax money out of my regular checking account to the Roth IRA account to fund my wholesale deal? 

For $250 I would probably do it myself or have one my regular contractors do it.  

Trance all of the income and expenses you are responsible for in report form and review that regularly with other people you trust and could help you reduce your expenses and possibly increase your income. 

Typically, you assume the balance as a wash with you and the seller and no escrow refund is due

I do follow up regularly. 

But have a regular evening schedule to help yourself and your contractors who know and understand your goals.There are a few things for you to do after you select your niche and market area and before you start making offers.  

He quit his regular job about 2 years after he started.You may have allready been in contact with him.  

Once these are complete we'll be moving full speed ahead on the regular repairs.

If it is the support of a supposed lifestyle, it is probably more important to identify the amount of money needed on a regular basis to support that lifestyle, and work towards that.

I know in a regular sale at least in MA its typically 1,500.