For the first deal and escaping analysis paralysis, I'd recommend just going with a pretty low cost property which might not have much upside but on the flip side will limit the downside and you'll get much faster/better learning experience jumping in

.  -- this is just the opinion of someone who's done a lot of research and works in a related field.LLC upsides - the can limit your legal liability if you're suedLLC Downsides - you have to keep all of the money total segregated, they increase your operating costs and complexity, they increase your costs to borrow, they can be legally challenged and pierced - particularly if you make any miss steps.Umbrella Policy - it's cheap to get a large commercial umbrella policy, and it keeps your operating model simple (with everything under your name).

I'm looking to purchase some multifamily buildings in Ontario, preferably looking at around 10 units or so.I'm analyzing some potential deals and there are some well-priced properties, but the downside is that they are severely under-rented (for example, they're around $750 average, compared to market rents of ~$1,300).Anyone who is familiar with Ontario knows the regulations are heavily skewed towards tenants, with tough eviction processes and rent controls.

The upside to low appreciation is minimal downside risk for events like this.  

But there are plenty of downsides also, which I really won’t get into here.

The downside to the commercial space is that interest rates are higher, PGs are generally required anyway, and you can run into issues with minimum loan amounts (i.e. you got a deal at $25K but the lender only does deals $50K and above).  

Cost of property: $38,500 Estimated Remodel/Repair: $5,000Total Cost: $43,000HOA Fee: $295/monthProperty Tax: $65/monthProperty Managerment: $80/monthEstimated Rental $800Estimated ROI (10 months): 8.28%Estimated ROI (12 months): 9.93% Monthly Dollar Value Return: $360The down side is, appreciation around this property is very low...

Using security for rent has its down side and expecting people to pay it back in addition to the rent when things normalize could take awhile.  

I try to limit my down side and buy on actuals.  

Only downside I see is that the monthly payment of the loan (which is fully am) is higher than the monthly return from the note fund (which is interest only),  I'd be out of pocket around $500 a month, but after paying myself back, I'd have 4-5k left over as profit at the end of the term.