I agree that DealCheck (or the BP calculator) does not provide enough tools or functionality to analyze those types of transactions (yet).But I would argue that it does a great job at analyzing more traditional buy & hold SFRs and multi-families, as well as flips and rehab projects. 

Thanks to God I have a well paying job and plan to use that income for any issues that may arise like vacancy or maintenance expenses.

You may also want to check the Columbus OH market - great macroeconomics with lots of job and population growth along with major companies developing here that drive strong rental demand. 

I work a full time job at a wood shop building custom cabinetry.

Year 1, I intend to keep my W2 job while i work to get my small business going.

i would:-get the highest paying W2 job you can-save up enough to buy a house hack-house hackwhile you continue to learn and consider the other possibilities you mentioned.

If you like your job, and your goal is to create long term wealth through equity then keep the property, fix it up over time, and in the future you will be able to rent it out for profit.

It's your job to create a buffer between the tenants before they start fighting as well.

I was an electrician for over 20 years with my last electrical job being shop foreman for a custom electrical control panel shop and UL 508 specialist.

In my day job I’m an ops professional who manages a tech stack and efficiency is important.