Great...just what I want from my real estate workshop...."

Hi,Since this is where I first learned about investing in real estate I thought i'd come here first. 

My brother and I, both out-of-state investors, recently acquired a long-term rental property in the Boerne area (near Leon Springs). We’re focused on building a strong network in San Antonio and its surrounding areas ...

To have a “job” that you in effect pay to have will get old real quick

Buy real estate as a "real estate professional."3.

The area of which I am green in is real estate investing.

Timing  really  will depend on what your plans are .... eg.. 

Then how much more you do should be determined by what the cost to upgrade things would be versus how much rent you can get if you do them.Separate entrance sounds really expensive depending on your homes' layout.Egress window might cost you too.As for a kitchen, its a small one bedroom in a basement so it isn't like you're going to be getting families renting the place. 

Depends where.

From reading your post, it seems that your monthly cashflow might be in the negative with all expenses considered.If you don’t go with the above, then you’ll be dependent on whatever you have set aside for cash reserves to keep the townhouse running.