@Paul Scavello, something doesn't sound right about this.  

Include appliance replacement amortization in your deal breakdown.

The challenge arises as the city permits only true divided lite windows, leading to a cost of $40k for 4 custom-built wood arch windows to replace rotted ones facing the street.

Your replacement property needs to be held for investment or associated with your trade or business. 

Even the heavy duty stuff, most likely going to need to replace every 2-4 years whereas plank will probably cost way less going forward on turns.

Sounds like a space you can throw up a hot plate and a small sink and you'd be renting out a part of your home in a week or so since it is already a permitted portion like you mentioned. 

Would I want to remove the home-owners insurance and replace that with a Land Lord Insurance policy? 

As a Cap Rate is indicative of the risk involved in owning the property, you want to focus on doing things that make your investment less risky if a bank ever had to take over.You can make your investment less risky by doing some of the following things:- Convert all month-to-month tenants to annual leases- Implement strict minimum rental criteria- Add security cameras- Make large capital and preventative improvements (fix drainage issues, install water pressure regulators, replace old HVACs...you get the picture)- Essentially, prove with action that you are caring for the property on a long-term basisThe only way this is effective is if you document everything you are doing as well.

One with 90+ members is great because it affords the HOA a lot of economies of scale with vendors thereby keeping HOA fees lower.Review the HOA financials and make sure they have a substantial reserve that would cover a hail storm deductible and/or other storm damage.Read the Bylaws to make sure they're rentable and check the pet limitations.Check the common grounds for any big ticket items that may need replaced soon.

I’m gonna be totally honest with you, it’s extremely hard if not impossible to replace a full time 40 hour a week with rental income at least in the shorter, it’s the type of thing that helps you retire a little early and have a buffer in retirement, my grandmother has been in poor heath for years, those properties have allowed us to give her the best care possible, if you don’t already own a home and feel comfortable with your budget and the ability to live in that house for  at least a few years, I’d get started on that don’t even need to over complicate it, find a budget, find a house you like and can see yourself in at least for the medium term buy it.