I know I could have a family member co-sign a mortgage with me but not sure the best way to approach that conversation and what incentives I’d be able to offer to make it worth while for them other then their “familial duties” haha. 

He's helping me to narrow down a potential multi-family property that I will be house hacking, (the deadline I have given myself to be in it is May).

if you want to buy a vacation house for your family, and you can afford it, and you'll occasionally rent it out - that's great, it's just not an investment. 

In your case of a fourplex, option 2 should get you a better deal.I would also agree with Bill on how the number of units may not correlate with the value of the property unless it is a large multifamily complex, and sometimes a fourplex or several single family houses would give you better returns. 100% We always recommend conventional first until you can no longer qualify for those. 

Investment Info:Single-family residence other investment.

Family committments can be pink (or whatever color), money making tasks (green), follow up for leads/lead generation (yellow).If it's on my calendar, it exists.

The median price is well-under the national average around $285,000 for a single family home, however there are great cash flowing assets even closer to $100K (or below!). 

However, not one general location is going to help you determine whether it's a good market for multi family or single family etc.The one true way to start looking into a market is talking to an agent who knows the area.

You can quickly see why looking at this graph - https://www.visualcapitalist.com/buying-vs-renting-house-in-...You can see how in 2015 the average mortgage was cheaper than the average rent, so it was easier to make the math work with light value add and just buying single family homes.

Do you want to do Single-family homes or Multi-family?