I'd really like to find something within 15-20 miles of the Andover area as the commute from Central MA daily has taken it's toll on me over the years.My budget is about $325k with about $10k down, although I have been approved for upwards of $400k on a single family, and most calculators online state I could afford $450ish, but I'm not sure i'm comfortable with a mortgage that high.Anyone from this area will be aware that it's slim picking if at all in this area for those prices.

Already have used this and as a newcomer, there's a lot of value in referencing this daily to become more familiar with the common terms. 

I would imagine you could make more money as a daily rental as compared to a regular month to month or year lease, if you can keep it occupied.Estimate I received from the city for all building permits for a garage conversion ADU was $3,500, with $1,500 of that being a fully refundable (with receipts) recycling deposit.  

I recommend setting up keyword alerts for each area as they are discussed in the forums daily with advertisements posted in the BiggerPockets marketplace hourly.One thing to note when looking at the individual markets, you can make or loose money in any market.

You should always ask permission to follow up when talking to prospects that do not convert.If you never connected follow up daily for a few days then weekly then monthly until you are no longer in that business. 

I have read several investing books and listen to investing podcasts daily. 

Good luck and keep taking DAILY actions, no matter how small.

I would sell and look if you can get a similar deal where you guy something for $600,000 and then get the value to $880,000 or close to it if you can.Looks like that might be the money maker instead of collecting the daily income.

@Nicholas Welch sounds like you have a great plan and are taking the necessary daily steps to achieve your goals. 

I can set you up to receive properties in the neighborhoods your looking for on a daily basis.