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To who this may concern,To discuss any matter in depthYou can reach me directly at my email on my profile page(biggerpockets wouldn't allow me to comment with my email here).

Would it be better to start with SFHs or dive directly into multifamily?

For example, I often see Buyers purchase property thinking there is a $1,000 deposit but then the tenant claims it was $2,000 because they paid the last month's rent.

You want to be working directly with the handyman, not the "GC" who is delegating and not doing any of the work.

If you buy in a market that does not yet have rules on STRs, they will someday and you don't know what direction they will go.

Yes, if you know the lenders who do not care about seasoning, no if you do not or get the money and season it so the deposit can't be seen.Now, that is a nightmare scenario and let me tell you why. 

I’ve already found some potential buyers interested in the deals.However, one buyer has recommended that I terminate my contracts with the owner and instead work directly with them.

But I also realize many people choose the direction of Appreciation first.In my hometown market (not Pittsburgh, but central NJ area), few small to mid size multi family properties could come close to cash flowing positively.

I have had luck with doing direct mail marketing for some of my past clients that wanted a certain area or neighborhood, you'd be surprised at how many sellers don't want to deal with showings and everything else that goes into listing a home.