@Christina Galdieri You can absolutely 1031 exchange into multiple replacement properties.

We don't need sprinklers here, but if we would, I'd either do that or replace the lawn with gravel or something else maintenance free.

My primary goal for investing in real estate to grow my wealth and generate a bit extra income- not replace my day job.As the first investment, I want a safe investment with a goal recycle my down payment for a second property within 12 months and focus on learning & long-term cashflow/appreciation.

So, if a tenant broke a window and it cost $300 to replace, you can simply add that bill in apartments.com and that way its all tracked where everyone can see it and track it. 

I try to pay off all loans as fast as possible because I feel like money wasted on interest is overlooked sometimes as people only focus on the amount of money coming in rather than the amount saved.As of today, I'm just focusing on establishing the best systems to analyze the markets, find properties, get financing, make wise renovations, and manage my rental properties.

Do you save three months of vacancy for each unit and $50,000 for the roof replacement?

You can replace the windows.

I wouldn't have any interest in buying something like this to hold since it would be so far negative cash flow wise on a monthly basis.

No benefit tax-wise. 

Best...Make the wiring replacement a contingency.