I talked about this in some detail in my BiggerPockets book Storing Up Profits on self storage.

Yes, the more deals you do, that are profitable, the more money you make. 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Boston is expensive just as any other major city so you might have to pivot outside of it. 

We share the profits and split losses if any 50/50.  

The majority of the investors at these local meet ups are either new or they've only done a handful of deals.

That could mean working with an investor willing to fund the deal for a share of the profits or starting smaller with a house hack or live-in flip to build credibility, or putting sweat equity into a deal with a partner to learn and build your track record.

An LLC shields personal assets from business liabilities, while S-Corp taxation allows you to reduce self-employment taxes by taking a reasonable salary and distributing remaining profits as distributions, which aren’t subject to payroll taxes.

It's tough to give a definitive answer without knowing your specific investment goals (cash flow, appreciation, etc.) and preferred strategies (BRRRR, wholesaling, etc.).However, since I'm a Cleveland native and active in the real estate market here, I can offer some insights on why Cleveland could be a good fit:Affordability: Compared to many other major metros, Cleveland offers a relatively low barrier to entry.

My tenants had late payments, but they were eventually made whole—credit where credit is due.Another standout moment was in 2021 when a major winter storm hit the area.