You put $287k in the bank and earn $14k/yr.

First impressions matter, and if the outside doesn’t match the effort put into the interior, it’s a deal breaker for many.

I’m considering offering the seller 85K, the realtor 12k and then put in around 35K to get both up and down units rent ready(might be able to do it cheaper, especially since it’s likely a rental).

My thought behind it was to simply get rid of debt and take on less risk  sure, if you are deleveraging across the board but if you are going to turn around and buy a new property with leverage that does not make sense. 

As far as home office no longer being an IRS "red flag" I guaranty that if you put a home office deduction on a personal return on Turbo Tax it will move their audit risk needle.

That could mean working with an investor willing to fund the deal for a share of the profits or starting smaller with a house hack or live-in flip to build credibility, or putting sweat equity into a deal with a partner to learn and build your track record.

- If they do not reply or approve, then we move forward with more risk.

Alan Ceshker: Austin, Texas 78731 to have him put that together for you.Be sure to ask what the drawbacks and risks are.

You do the work and they put up the money.

Understand the strengths in your market, what does well / has lower risk since you're just starting out?