I didn't feel comfortable with it.After I left teaching in 2011 I felt the weight of a 100lb pack taken off me.

A good agent will sell you and your offer to the listing agent effectively, and most good investor agents are known as such by the listing agents, and carry a lot of weight that things will get done smoothly and professionally. 

Let me explain -In January I had a freak gym accident - I've never been a gym goer but with the advent of my 2nd child I decided it was time to get healthy for my family, I was 315 pounds and really over weight so over the last 8 months I've lost 82 pounds but that's a story for another time.

In my honest opinion, I think you may be putting too much weight on the gender thing.Sellers like to work with people who1.

People don't have savings and if you have tenants that always pay and stay a long time, then they're worth their weight in gold.

They are worth their weight in gold as a real estate investor.

But if I can get it within the first 20 days that would be spectacular, and if the BiggerPockets community has the answer for this then it would be worth it's weight in gold. 

@Troy MitchellWelcome to BP, I am new myself as a Pro member, so I don't know how much weight my welcome carries but here it is anyway.

I could see in the case of a TRI or FOURplex could shoulder the weight of 1 unit.

A HELOC should be explored in addition to a cashout, lots of variables here as to what the best route is.I wouldn't put much weight into the neighbors, this is common and as investors we build thicker skin as we go forward via pesky neighbors and tenants. =)I would recommend your plan involve you not paying MI on your new purchase, so coming in with 20% down + would be my advice.