Otherwise it’s time for a big/serious talk about making such a HUGE and basic mistake. 

Don't talk yourself into a place because of personal use.Buying a $475k condo that brings in 35k in gross rental income will lose a lot of money.

Whether it’s finding deals, running numbers, or just exchanging ideas, I’m always down to talk shop with like-minded investors.

. - I was in a VERY similar situation here in Chicago, but I had less experience working on my own than you.I had a piece of land that I owned free and clear, but since I didn't have any development experience, most of the banks wouldn't talk to me. 

Here's what I would do:Option 1- Talk to the lender to make sure that the buyer is strong.

No verbal talkie-talk on it, no, send it over WITH the amendment for them to sign. 

Looking to talk to someone who’s had experience adding a bonus room/sunroom in San Diego.

You can make straight Roth contributions or convert cash as you’re talking about but you can also convert assets from pre-tax to Roth.

I hear Dave Meyer sometimes talking about Green Bay, Wisconsin and a few other markets on the podcast where he's saying you can go on Zillow and find some deals that are cash flowing.

If you ever want to talk more, I'm happy to connect.