Depending on your budget to purchase and renovate, the BRRR technique may a route you want to strongly consider.

For example, if you have a person on the 3rd floor that cannot use the stairs and you have a vacant unit on the 1st floor, you may be required to relocate them to this unit during the renovations.

A hodge-podge of updates over 100+ years have left the houses with awkward spaces and outdated everything.The larger house is 1,625sqft duplex with a 3 bedroom unit on the first floor and 2 bedroom on the second floorThe small house is 1,150sqft duplex with 1 bedroom on the first floor and 1 bedroom on the second floorAsking price (FSBO) is around $240k for both (7 bedrooms total, 4 doors) but I'm fairly certain there is plenty of wiggle roomThese houses need *complete* remodels.

But not as many venues can handle larger affairs of 200-300 guests, so there's less competition in that niche. - Do you have adequate parking?

We renovated the commercial space and are about to get a tenant in.

Basically a gut renovation.

After two renovations in other properties, I sold my own apartment in 2007 through an incredibly complicated series of contractual maneuvers designed to skirt EU  banking regulations, and the bank was as in on it as the buyer was. 

Renovations and maintenance are costing most of my imagined profits now but I believe I'll get to a place where the income will build.

I'm ok with tenants leaving because rents are low and this gives me an opportunity to renovate one by one. 

Fix/renovate property.