You'll have to look at the income and expenses to predict whether your cash flow will improve.

I'd also suggest self-managing your first property to maximize cash flow and learn by doing for any future investments.

You can get between a 12% and 15% cash on cash return each year pretty passively.

Those remote flips and high cash flow rentals are so tempting on paper, but they rarely go well in reality. 

Are you looking for cash flow/appreciation/a little of both?

I've been buying SFH's out of state all cash as long term hold rentals.  

you could take $300K and purchase one property for cash. 

If it sold for $120K in 2007  , and your rent is $2000 a month , the landlord is probably cash flowing rather well .   

House hack another property with a low down payment loan and use the remainder or the proceeds to either renovate or purchase another investment property?  

my condolences on your recent lost.there are a few ways you can do this, as mentioned above you can take a heloc on your primary residence which will give you a second mortgage, first mortgage payment wont be impacted. you can do cash out refinance which will give you one mortgage and payment. it will pay the old mortgage and give you money in your pocket to pay for the rehab.or you can do a renovation refinance which is similar to cash out refinance but we would contractor involved  as part of the refinancing and they are paid through the loan