Plus a really nice upgrade in communication as well! 

They instead focus on fully gutting their projects and install entirely new kitchens, bathrooms, fireplaces, accent walls, etc. and any exterior or mechanical upgrades necessary.While I understand this whole hog strategy, part of me says this will end up increasing the value of a home so far beyond other homes in the surrounding area that it wouldn't sell for what it's likely worth.

That can happen if you buy a home that needs a little TLC or renovations and after the upgrade the new ARV might put you at that 85% LTV or lower, possibly even be able to take cash out.As a first time home owner you can use FHA 3.5% down or Fannie Mae 3% down (single family).

Buying an existing place that needs upgrading might be more sensible but it will still cost a lot of dough.Plus the purchase of the catamaran.

Given your situation and concerns, here's a breakdown of considerations and advice:Pros of Renting Out Current Home and Buying a New Primary Home:Living Condition Upgrade: Moving to a larger, newer home with boutique features can improve your living space.Rental Market: West Town in Chicago generally has a strong rental market, which could provide good rental income from your current home.Portfolio Diversification: Adding another property to your real estate portfolio can enhance diversification and potentially increase long-term wealth through property appreciation and rental income.Cons and Concerns:Interest Rate: The current interest rate of 7% on a new mortgage is high, and there's uncertainty about future rate decreases.

This is my first project that I'm doing on my own - 425sf addition + upgrading existing house.

We will upgrade from a C market to an A/B market.  

Are you upgrading to a bigger home?  

It got worse.Unlike QB Desktop, the online subscriptions limit the number of classes any entity can have, unless you upgrade your account.

Insurance is WAY cheaper for a new build, as are utilities, because the newer homes are more energy efficient, and also have less need for immediate upgrades.