If your intent when you purchased that property was to hold it for productive and something is forcing you to change your intent and sell then you could simply do another 1031 exchange and continue to defer both tax and depreciation recapture.The tax never goes away until you either die or sell without doing a 1031. 

Deferred maintenance preferred since we can renovate a home for a fraction of the cost.

Understanding how and when to use 1030s, 721s, and DSTs (both Deleware Statuatory Trusts and Deferred Sales Trusts.

I budget 10% CAPEX and 10% maintenance and still struggle early on because things break and there is deferred maintenance.I see nothing about water/sewer, property management, etc.The report has already told you how this will probably go:50% Rule Cash Flow EstimatesTotal Monthly Income: $3,200.00x50% for Expenses: $1,600.00Monthly Payment/Interest Payment: $1,958.06Total Monthly Cashflow using 50% Rule: -$358.06Don't ignore this.

There's a lot of deferred maintenance and my favorite thing was the inherited tenant.

Choosing the best one depends heavily on your long-term goals.Brooklyn Quads on the low end are in the 800-900K range and these are properties with: non-paying tenants; tenants paying way below market rent; deferred maintenance; locations in C/D areas; etc.

I agree that its a lot better to get this done right while i have it open, instead of deferring it and having it bite me later on. any tips on doing stuff like this, or resources, etc, would be much appreciated! 

(In other words your purchased property will probably have to be twice as expensive to fully defer taxes.)

It's hard to stand out.There are some owner-occupied segments with people who share motivating factors for selling their home.Seniors with Long-time Ownership: often ready to downsize or transition to assistance.Homeowners with Low Financial Stability Scores (FSS): Struggling financially and likely ready to cash in on their asset.Both these categories have additional advantages in that they probably don’t haven’t been updated and may have deferred maintenance.

Cured deferred maintenance (overgrown landscaping, peeling paint, tilted mailboxes), cosmetic work including interior and exterior paint, rebuild of patio fencing, striping of parking lot.