Realtor Opinion of value What was the outcome?

If you're going to work with an agency, you should work with an actual agency rather that is unbiased in my opinion.

@Brice Alef-Torrisi putting each property in its own LLC is usually overkill.Getting a bank account for each LLC is typically something you need to do to avoid "piercing of the LLC corporate veil" (actually depends on tax selection you made for LLC), but is also overkill.You haven't indicated how you are holding the deed for the latest property.If in your name or same LLC, you don't need a separate bank account.If in separate LLC, you can create a Master LLC, have each property LLC hire the Master LLC to manage their affairs, and just get a bank account for Master LLC.This is an opinion, not advice, so lookup CPA Frank Alcini in Troy for expert advice.

I had to take a 20 year corporate engineering detour to get back to what sparks joy for me.

The best opportunities in the Mansion are the parts where it borders an area that is at higher scale in my opinion.

Everyone will have a different opinion on this but personally I'm not a fan of new construction.

Here’s our OPINION for the Metro Detroit market (use as a template for your target area!)

Hey @Dalton Foote - I highly suggest  using a renovation loan and house hacking a multi-family if that is possible with your current life circumstances.The 203k and homestyle renovation loans are just amazing products and drastically help you reduce your risk, in my opinion, because you are able to leverage the cost of the entire renovation with such a low down payment loan.We work with a lot of clients who use these products in Chicago, and no matter what, in the long term, they gain great equity.If you aren't able to house hack - the process is essentially the same, but just with more money down with hard money or conventional construction loan.

Lastly and then I will stop rambling... and this is just my opinion. 

The tax rate difference from from long term to short term alone won't make it worthwhile in my opinion- add the 401K withdrawal penalty on top.