The first deal is always the hardest one, but the faster you get going the easier it gets.I would definitely talk to @Eudith Vacio she works for KW and I know she is doing some investing in NW Indiana, sounds like that could be a perfect fit ;-)Also, I am happy to talk or help in any way I can. 

@Tom Knox That's a perfectly valid 1031 with some really nice added benefits. 

I have waterproofed exterior stairs, decks and roofs/balconies over living space where it has to be perfect.

@TJ WatsonTo be perfectly honest I have not ventured to San Diego yet but clearly I need to based on all of these great replies!

While not perfect, I find Homewyse.com to be very helpful in getting a general idea on estimating cost. 

Also, being that it is my first property, I'm not looking for a perfect BRRRR. 

By the way, in case it changes anything - apparently it's perfectly permissible to pull out the $500k from Bank 2 as soon as the transaction has closed.

And keep in mind, the insurer has perfected title as insured so it's fully performed its obligations, it won't owe you anything else. 

Investing is not an art open to interpretation but a science that you can perfect in order to produce repeatable results.Understanding What constitutes a good deal, developing solid Due Diligence and Deal Structuring systems.

Worked out perfectly