Women on average are shorter, so understand there could be issues for some people even if you can reach fine.

I too, started under similar circumstances, my wife, who was then my girlfriend "encouraged" me to purchase my first home in 2011, best decision I've ever made and we haven't look back since.

Is there a wiggle room for accelerated depreciation for special circumstances such as this?

I have bought properties I intended to live in but decided to rent out instead, in my opinion there is nothing wrong with this, peoples circumstances change all the time.

But for the condition it was in and what it needs vs. price they wanted and my own circumstances,  not the best move for me.

In your circumstance (congrats btw), if you wait too long to cash out your available equity, that equity could go south just like the investment properties that you're hoping will be cheaper by the time you buy.ie. 

@Mike Trzaska inbound marketing is king under any circumstances...that said, I do believe direct mail has a place... and your approach to writing handwritten cards will yield the best results.

The tenant must make a rent payment as close to the actual rent as their circumstances allow.  

There are only a few circumstances where a cash offer is more beneficial to a seller.

@Kimberly Carver In normal circumstances it would be easy to evict a holdover tenant because it's easy to prove the tenant is not a legal tenant when the lease is active there is a burden to prove the tenant has materially broken the lease.