What programs/tools/resources have you found helpful for things like:Finding areas that are most likely to increaseFinding the best size or room numbers to optimize profitAny other areas that would be good to knowThanks in advance

In that situation, the dwelling unit is never disposed, and that is the essence of the dynamic you're trying to examine.Now, with the situation at hand, you're talking about a lot more than just scrapping the mobile home, so the optimal answer given the facts and circumstances would depend on a conversation with a tax advisor who excels in this area. 

It’s not a bad decision giving everyone you have stated but it’s certainly not optimal either.

Selling the existing SFR sounds like a pretty sub-optimal idea now :) @Austin Largusa investing out of state is absolutely on the table!

To be honest, 30+ minutes on a dirty CTA each way is not something I’m willing to do, I work 70-80h a week (that’s my “little sacrifice” already) so it is important to keep my daily routine optimized, and walking to work from River North/West Loop is not negotiable.That might as well mean that it’s better for me to keep renting rather than “investing” in an overpriced condo. 

.#3 Contact Local Contractors for Labor Pricing / Hire a GC to ConsultCall local Subcontractors and get budget pricing for common repairs on your typical rehab project.For example, call a roofer and ask what their average cost per Square of Architectural Asphalt Shingle Roofing would be on a 1,500 sf house, with a 6/12 pitch.Note: Some contractors will be reluctant to share pricing without seeing the property, but tell them you are just looking for a rough budget number you can use on future projects.You can also pay a General Contractor a consulting fee of a couple of hundred dollars (per house) to walkthrough a few properties with you and provide a detailed estimate of prices that you can use as your 'menu for future projects.#4 Compile Your Prices into a Spreadsheet or Estimating SoftwareOnce you start to get a better understanding of Labor and Material costs you will want to store this data into a spreadsheet or software that you can use to help you streamline the estimating process.The Book on Estimating Rehab Costs comes with a spreadsheet that you can use to help you populate your own database of labor pricing and material pricing.

.$3,000/month x 12 months = $36,000 annual ADU rental income$36,000 income – $5,400 expenses = $30,600 net annual revenue$30,600 revenue / $225,000 investment = 13.6% annual returnHere are some things to consider with regard to ADU amenities to optimize rents:Storage: ADUs are generally pretty small and usually don’t include a garage, so it’s important to include areas for tenants to store their belongings.

Just search out Lease Agreement Packages in the TOOLS menu at the top of the page.

Hopefully you can filter down from the doc type menu and see grantors that aren't big institutions.

Since my work allows me to go remote, and work form anywhere I can use that to optimize living in that area.