For what you are trying to achieve you'll want to stick to the suburbs and a few choice neighborhoods on the West Side of the city.

., San Diego, and others)—making it feel like a “natural” choice for a regional traveller wanting to get away for a short weekend. 

I'm sure it's a little more efficient in larger cities, but my market requires up to 60 days to get approval.Lower your expectations with Section 8 tenants.

If the community is well-managed and there’s good rental demand, a condo could be a solid choice.

Are you set on starting with a larger property, or would you be open to beginning with something smaller to build experience?

I feel a loss of direction and that makes it really hard for me to focus and build.Do we keep at building a portfolio of small multi family (very abundant in my market, very rare to find anything above a triplex for sale), with plans of selling the portfolio and 1031'ing into larger properties? 

Depending how much of the neighborhood is a hot zone for renting rather buying, and which Property type is performing better than the other (meaning 1bd 1ba 2 floor renting out faster and much more consistently than a 2bd 1ba 1 floor), you can make your choice of those factors as well as other ones that impact your decision for what you wanna do with your investment.

For example because New York is a generally more expenisve market, you have larger loan buy downs, bigger dollar appreciation, etc.

If I can replace the bathtub with a shower, I'd be able to make the bathroom feel larger.  

If it is a larger bank/mortgage broker, you should be fine.