The existing homes will be cheaper than new builds, so you might be able to find a deal due to price compared to new builds to offset the new build cost/repairs.   

Maybe you might want to see if your current lender for the existing HELOC is willing to extend your credit limit?

It’s built for independent landlords and smaller portfolios, but it scales well if you add more units over time.A few features that stand out for portfolio management:Dashboard view – Track rent collection, leases, expenses, and cash flow across all your properties at once.Tenant tools – Screening, leases, and rent payments all in one place.Banking integration – You can connect your existing accounts or use Baselane’s banking to keep rental income and expenses organized (helps a lot with bookkeeping and reporting).Mobile-friendly – Even though there’s no dedicated app, the platform is cloud-based and works smoothly on your phone browser, so you can manage things on the go.It’s a nice balance between property management software and financial tracking, so you always have the full picture of your portfolio. 

So we know that scenario existed and worked Norada sold a bunch of notes funds went to Lopez and the rest is history. thats my WAG  Just my opinion I have no way of knowing if its true or not..

We are interested in converting existing properties into Shared-Ownership via TIC's. 

It's a seller finance wrap on the existing mortgage. 

We already own a home of our own and we're thinking of doing a Heloc in order to fund our first rental property and rent out our existing home but would that be wise?

Zoning & ADU ConsiderationsChicago’s ADU Ordinance applies if you create an additional dwelling unit beyond the existing count.If you stay at 2 units total (just shifting one unit partially to the basement), you likely don’t trigger ADU rules—but confirm with zoning since each ward can interpret things differently.If you want to eventually rent the basement as its own apartment, you will need proper zoning, permits, and a second exit per Chicago code.3.

I love the Shenandoah valley and think that it is a fantastic place to buy a STR but there are certainly some areas to avoid due to local regulations or local saturation in the market.

Namely, when he has to exist and operate in social constructs not of his making.