Since we have not worked with this group before, I am hoping to get some references.

If you are investing consistently, you will know what your market charges for the work needed. 

I've been reading a lot of threads on here pertaining to which property management software works best, but so far my understanding is that both of the above offer unique aspects that the other doesn't provide;  Would it make sense to use both?

There are lots of lenders out there that specialize in different things and have different workarounds. by working with the same broker, they'll understand where your priorities lay and since they have a better understanding of your experience, they can push for exceptions that wouldn't normally be approved.I myself am a broker so I may be a bit biased here, but if you do feel that your current broker isn't very good or that they are overcharging you then you can certainly explore other options.

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

Reasons to sell the seller on the Owner financing might be, because you are going to do a substantial rehab to the property, or that the property doesn't have any buyers, and this is a way to sell the property.Seller Financing works a lot better when there is not a realtor to pay, where a realtor's commission could be 6%, which on a $300,000 Purchase would be $18,000.An additional option you might consider if you are looking at purchasing this property to do a flip, or fix and rent, is you could propose seeing if the seller would partner with you, and you would secure a Private Loan for 50% of the sales price, plus the rehab, and if there is enough upside equity, you would probably be able to do a cash out refinance and pay off the seller that way.

Some key factors, or questions I often get from the investors I work with on the buy side for STRs, that you can focus on in your listing, are as follows. 

Then I would take the remaining money that you have and invest that into a multifamily building if you are inclined to put in the work.

I have been voraciously studying and planning and implementing for the past four months and have just completed my first wholesale deal (closes a week from today). 

I’d suggest checking the condition of the new property first—you might need to put in some work if you plan to live there long-term.While I’m not a tax professional, and you should definitely consult one, keeping your current home as a rental seems like a solid move.