By 2030, we want to have grown a portfolio of over 100 units, created a property management company that manages an additional 100-200 units, and, finally (and most importantly), we will have established a non-profit that is focused on quality, affordable housing that specializes in providing housing and resources at/on the "services cliff" alongside financial counseling and first-time home buyer education in our target area.Our target area is the Springfield, MA and Hartford, CT areas with dreams to expand to Central Massachusetts (Worcester, MA), Southern New Hampshire (Nashua, NH), and Southern Connecticut (New Haven, CT).Would love to meet up with likeminded individuals in our area!

This initial negative equity position consumes the initial cash flow.  2) the addition of the adu makes the property multi family and likely makes rent control apply.  

Second, I'd connect with some local hosts in your area also in addition to Airdna.

Real estate investing has been a passion of mine for time with my mother also having invested early on where I likely have gotten the love and desire to follow similar foot steps.I have taken last 6 months to educate myself and currently own a single family home as primary residence and would like to expand to multi family properties (2-4 units) for additional stream of income, not to mention potential tax benefits for long-term investing.Based on current living situation, I have a fair amount of equity established in my primary residency along with having enough cash to either pay off house completely or use towards investing in a multi family property.Given that I'm the sole source of income for our household with my wife being the home maker for our two kids under 2, trying to weigh out risks with getting started now or perhaps waiting. 

That is in addition to clauses that require anyone that stays more than 7 nights in 12-months to apply (then it becomes our choice if they are treated as a temporary occupant or tenant) and prohibition of subleasing.

Properties below this threshold present additional risks and more limited borrowing options.7.

Additionally, have a clear budget, factoring in potential repair costs, and ensure you understand the rules about earnest money deposits and closing deadlines.LLC for Real Estate Investing: Forming an LLC for rental properties can offer liability protection and may provide tax advantages, though the tax benefits are non-existence for rentals.

Many insurance companies do not allow adding a landlord as additional insured.  

In addition, yes there are property managers but very few want to manage my B or C class property for an extended period of time in the fashion I would if I was managing it or that a really good sponsor would.

If we sense there is a red flag, were asking them to upload additional documents like tax returns w2's etc.