I would recommend you make short question summaries of your current situation and post them on Avvo for free (takes about 1-3 days for Lawyers to respond) and break your situation up into short segments that way you have multiple topics and various lawyers giving you their opinion.I work as a junior accountant I'm sure my co-workers (CPAs) won't mind answering a few questions.post your questions here and I'll get you some feedback.

Does anyone have any recommendations for real estate agents who work with investors and property managers who work with investors owning multiple single family homes?

It is possible to close multiple loans at once but they are not designed for units that are platted together.

@Christopher Phillips, yes I have called multiple people through CL.Is there any other portal/website I should use for getting estimates?

Even owner occupied VA 4-plexes are around mid 4's.There are going to be multiple schools of thought here because there are multiple variables.On one hand you can refinance the VA loans into conventional.

The reasoning for this is that I can have multiple rented out instead of just one higher priced rental.

In my journey that i started in Jan 1 st 2018... towards financial freedom, i document multiple actions I take and analyze the process of investment and raising money. 

I don't think you will get far just throwing out offers of 85% on multiple properties unless you are willing to negotiate as well.  

So you don't really need a realtor to write the offers for you although im not sure the benefits of doing that since you don't pay any commission as a buyer.There are multiple ways to get access to the mls.

Can it cover Multiple properties and does it come a lot cheaper than having Landloard Insurance (Covering Fire, hazards, Wind... ) ?