It is past the tax assessment. 

Real estate investment can be incredibly rewarding, between the cashflow, appreciation, and tax benefits, it truly is the greatest wealth creation tool. 

You are so right about analysis paralysis 😁Not too concerned about mechanics though I would like to learn more about how to best use CRMs (specifically freedomsoft), but also would like to learn specifics regarding forming LLC structures and tax strategies 🤔

Hard to give good advice without more info, but since You are single no kids it's hard to beat buying a single family fixer upper and living in it for two years and then selling for tax free profits....I'm a big fan of Waltham these days $.02 

Some questions to consider:1) How much negative cashflow can your other income stream(s) support?

Also Seller hasn’t paid property taxes in 2 years which is a sign the property is in distress.

You filed two full year tax cycles and the numbers are similar (no greater variant than 1%) they maybe yes.Generally depreciation is added back as income BUT only the 40% portion you own not all of it.

Review your prior year income statement.How did your year go?

Kudos to you for doing something to create a secondary income stream. there are 5 income streams in RE rentals, possibly six if you do things a certain way.The reality here is your model (buy box) is suffering from too high an entry and too high a cost of capital.

Usually the numbers don't work to build in these neighborhoods, unless government tax credits, etc.Do you see the problem with your two statements:"The turnover costs could/will be high"and"How much more damage could they do?"