That tells you mainly want buyers are hunting for and purchasing.

With those costs a new build with the purpose of selling is likely not worth it. 

You won't have the options that you have here in Austin, mainly because Portland is Tenant Friendly City and Pfugetville is Landlord friendly.  

You have two things going on, and they are unrelated for tax purposes:1. doing rehab and paying contractors2. borrowing money from a HM lender

I don't have personal experience with it, but when the app was first developed, I contacted the developer and put the app through a fairly robust test usage to see if it's something I would want to recommend to my clients (I'm a CPA).I think the app is great for its intended purpose and I do recommend it to my clients now (and have for about 18 months now). 

My main question is will I be happy in 10 years that I bought this property?

Main thing I would think of if you are targeting families are things like pack and plays, cribs, gamerooms for kids, etc. as well.

The purpose on my end was to have an investment that could be used during retirement as cash flow tax free.

Here are some rules:  https://www.nerdwallet.com/article/investing/roth-ira-withdrawal-rules#:~:text=Contributions%20can%20be%20withdrawn%20from,made%20without%20taxes%20or%20penalties.I agree that you shouldn't let the tax implications be the main driver of your decisions, but you do want to be aware of the potential tax implications because Uncle Sam will want his money.

The IRS views it as taxable income because it’s not being used for the purpose of deferring taxes under the 1031 rules.For example, if you sell a property and only use part of the proceeds for the next investment, the leftover amount (after paying transaction costs, etc.) is taxed.