You'll have to paint and make other upgrades and repairs when each tenant moves out, not all of it will be covered by (or applicable to) the security deposit.

Where can we run the applicant's credit score?

When you are wealthy, tear it off and hang drywall, tape and texture.4) Replace the appliances with fresh ones from Craig's List.5) Don't forget to tune up the curb appeal as well.

If he handles 40 flips a year we are talking 100k.Should it matter that I can get 200 applications if i put this job on craigslist at 40k?

I will provide them a recent bank statement showing a balance greater than $300,000 and offer to pay a year of HOA fees in advance, and I will offer to have a third party investigator do a background check on me to prove that I do not have a criminal record, given that I am paying cash there is no logical legal reason why they should refuse my application, but this application process may have little to with the law.

Buying quality homes that better tenants want, helps increase the quality of applicants. 

Increase given today may not be in effect until Aug 1 meaning increase (if 30-day notice is applicable) would be effective Sept 1.My guess is that MA Winters start stalling market rentals in Oct which means you may be risking a very long vacancy window if either or both tenants choose to vacate. 

This is another place where a building inspector could help warn you about any major repairs that may be coming due in the near future (new roof, new heating/AC, etc)Property Filter strategyProperty must be in price ranges of 25000 to 675,000 with the maximum including repairs.Must be maximum 25 years oldMust NOT have nearby UN-clean properties Ex/ non maintained lawn, crumbling roof/structure, torn gates, abandoned cars and possible current crime related houses Must not have major issues or structure issues,examples include an unstable foundation, and big holes in the roof or walls.Seller must be willing to pay 50 percent closing costsMust not have taxes that go over 8250 annually Must have at least 25% in equityMust have the potential rent value of at least 500Must not have more than 2 mortgages on the propertyDocumentation to ask the seller for:Leases/rents for the past year, Tenant applications and screening procedures, tax returns for the past 2 years, also income and expenses for the past year, current rent roll (including unoccupied units, unpaid rents, and concession losses), List of improvements on property in the last 10 years.Documentation of all loans against propertyAvoid all illegal conversions or constructions.Avoid houses with no electrical wiring or AC or plumbing or if these criteria are severely damaged.Property must have cash flow of at least a total of 100 dollars.Plan for Financing At 18 years of age I will start investing in Multi homes with a loan called 203b mortgage (an FHA loan).This will allow me to only put up 3.5 % as a down payment and have a very low interest rate of around 3.5-3.9%.This loan requires me to live in the property for 1 year + though and have mortgage insurance, and so I will live in one unit while my other 1 or 2 units are rented out while I attend college.My down payment and closing costs will be from saved money from jobs in fast food and other work areas from beforehand.I will use 30 year fixed rates.Steps to take in the whole process:Have my attorney write up my contracts beforehand which include ways to exit before closing, financing terms, closing costs being 50/50 split , make sure the sellers future property info is accurate and reliable or else he is accountable and everything else he/she recommends Have my loan prequalified beforehandMake a lowball offerNegotiate until an offer is accepted or you have hit the buying price limit, or the 70% ruleOnce an offer is accepted inspect the house thoroughly by an appraiser and an inspector and take lots of pictures and videosrequest these forms:Leases/rents for the past year, Tenant applications and screening procedures, tax returns for the past 2 years, also income and expenses for the past year, current rent roll (including unoccupied units, unpaid rents, and concession losses), List of improvements on property in the last 10 years.Documentation of all loans against propertyIf the deal is still sweet, go ahead and continue with closing and finalize the deal Hire a property manager with at least 3 recommendations and question him about      these areas of work, also ask for a complete list of all past clients contact numbers.

This is somewhat flexible depending on what is to be taught, teaching carpentry is one thing, teaching what law is applicable or teaching conceptual materials is another.   

college vs up and comingCollege will likely have a lot more turnover and be more time consuming with make ready between tenants, but will always have a steady supply of applicants with parental co-signers...