Downspout depend on the section, the lower ends are very easy to replace, if it's higher up then it's a bit more involved but still not hard. 

Finish the basement into a legal apartment and then maybe rent the 2 car garage as storage/secure car parking.People in the city are always looking for secure places to park their cars depending on where the place is.

(depending on your current financing, the limit is going to range up to 90% LTC in most cases)2.

And depending on the offers I get for selling or renting, I can decide whether I want to sell the property or rent it out. 

You will run out of money for down payments quickly buying rent ready rentals & the STR income can fluctuate greatly depending on the season / state of the economy.

Depending on what brokerage you join you will have monthly office costs, and pay a percentage of your commissions to the brokerage.

@K S.It might depend on if your PM company does all the management.

It depends on what you want to do and how much time you have to devote to real estate investing. 

Both times the tenants had renters insurance in place which took care of the issue so my client (the landlord) did not have to get involved nor make a claim on the landlord policy.We are very much in a hard insurance market right now - many carriers will not accept a new policy from you if you have a property or liability claim within the last 3 to 5 years (depending on the carrier) so you really don't want to make a claim right now if you don't have a large loss or can get it sorted yourself.

But this all dependent on finding the right deal, right neighborhood etc.