I've heard of people spending more time and money on the land, utilities, roads, and common areas (especially if there's a bath house) than the units themselves.

For a complete beginner that is trying to jump into their first deal with absolutely little to no knowledge (obviously read books and countless videos, etc), when is a good time to start paying the $100 a month to utilize PropStream?

Section 8 will deduct utilities that the tenant pays from those figures.David KrulacBigger Pockets Podcast #82   

We are also getting a forgiving loan of 30k for the duration of 10 years from the county for 1 unit if we rent out the 1-bed basement unit to a household with income less than 100k and at the rate defined by the city )(~1183+ utilities) for a 1 bed unit.

High utilization rates from other cards that weren't even the same company.So beware.  

Should I have my tenants pay all of the utilities?

Consider targeting properties that have the potential for appreciation in value, as well as options for utilizing tax-saving strategies such as cost segregation and 1031 exchanges.

Additionally, it can help maximize renovations and improvements.A Cost Segregation study is an IRS approved federal income tax tool that increases near term cash flow by utilizing shorter recovery periods for depreciation to accelerate return on investment.

Then if they don't leave after the 30 days you could proceed with the holdover eviction.You should NEVER have the utilities in your name.

I expect the property to appraise for 300k after renovations.After renovations, I plan to find a roommate and rent one room for $800 a month and split utilities or $900 flat.