you aren't the moral police, or the regular police.. you're a landlord.      

Do not cut any corners to make a deal look better on paper but not in reality.Track all of your income and expenses that you are responsible for and review them regularly (in report form) with people that can help you possibly reduce your expenses and increase your income.  

The Bigger Pockets book store if full of great books: https://www.biggerpockets.com/store

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.  

The Bigger Pockets book store if full of great books: https://www.biggerpockets.com/store

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. 

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.  

If expired, kindly ask that it be currentWhat about Big Box Stores, or Theme Parks, etc. that allow Service Animals.