-If it's determined that your Alderman would be supportive of your 'plan', and you've already connected with a local architect, you'll then want to reach out to a zoning attorney.

That will largely help to determine the right fit in the landlord market for someone with a portfolio. 

Lease Terms: Determine a monthly rent payment that covers the HELOC repayment (interest and principal) while providing some positive cash flow for you.                    

He believes he can find all that he needs to know on the internet.

• Should utilities, internet, or services like snow removal/lawn care be included, or not?

As others have stated, you have not provided enough information to determine whether this is a good deal or not.

For me, the first pass at underwriting is simply about determining if a deal is worth exploring further.In the current market, I’d say 9 out of 10 deals are dead on arrival.

From my understanding, as long as you intend on doing a STR when you close, there are no rules against changing your strategy after closing, especially if you find that something else is more profitable.So in our case, the lender determined an STR would bring in ~$3500/month (with all of their conservative factors), but now that we operate it as a huge 3300 sqft Co-Living property, it actually brings in $7000/month.

Newer buildings now have state-of-the-art amenity packages with pools, gyms, co-working spaces, high-speed internet, and community gathering spaces where savvy property management groups will have apartment building events to encourage this sense of community, all being a level of convenience and neighborhood community people cannot get anywhere else.

I am a complete rookie zero experience, zero properties and highly determined to get into multi-family investing.