.- Cities like Toronto will levy another tax (Vacant Home tax) equivalent to 1% of the current assessed value of the property if the property is not occupied (rented, owner-occupied, family occupied, all count as occupied)- Land Transfer Tax: while the Province of Ontario charges anywhere between 0.5 - 2% of Land Transfer Tax when your transaction closes, you should expect to pay this amount twice if the property is in the City of Toronto .

Doing a 100+ unit deal is totally doable as your first transaction.  

As you probably read through the comments on this thread, there are many moving pieces, costs, and folks involved in this transaction. 

Since you mentioned REI Hub, I worked with REI Hub in the past and they had the same connection issues but their CEO is usually good about making quick updates to create a better user experience.That being said, there is no perfect solution out there regarding bank feed connections so I'd go with one you know and ensure the accounts are linked on a weekly basis to be confident every transaction is flowing through without interruptions.

On the other end of the spectrum you have those teaching others how to syndicate larger transactions.

. $275K acquisition  and you believe a 40 year amortized loan is necessary to make the numbers work, this transaction may have bigger problems.  

Focus on learning how they generate leads, negotiate deals, and close transactions.

A good accountant can determine how to account for the 70k received in the best tax advantaged way that makes sense for the transaction.

Be wary of the facebook groups as most folks will have a "pitch" or just see the possibility of a transaction.

If you sell the property, a lot of the $107K cost will be eaten up in transaction cost.