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All Forum Posts by: Jessie Dillon

Jessie Dillon has started 12 posts and replied 304 times.

Post: Self employed , motivated and really confused

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

hey! i'm not far from you, i'm in hopedale ma. i'm also fully self employed, so lending can be tough! i've graduated to commercial loans, but you can't do owner-occupied with those, so here are your options:

- traditional owner-occupied loans with self-employed-friendly brokers
- private money

a private lender would be wacko to lend on someone's primary home, but it has been done!! 

that first option is more likely to be the route you take. you can still totally use an fha, usda, 203k, or naca loan to get into a primary with 1-4 units that you'll live in for low money down. BUT using the right mortgage broker is key. when i was buying my primary househack (2-fam), one regular bank lender told me i was preapproved for 275k. it was laughable in this area. another broker who i had just closed a different property with, asked me how much the property i wanted was, and wrote me a preapproval for that amount. and yes, we closed. some lenders just don't understand how to work with entrepreneurs / househacking, and others do. one broker i love for this type of thing is vernon miles at milestone mortgage solutions. give him a call!

Post: Best Tips for Preparing Your Current Home to Be a Med-Term Rental

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

love what you're doing! here are some tips:

3bed MTRs aren't as in-demand, so don't be spooked if you have longer periods of vacancy. you could consider doing MTR by the room, for all traveling professionals, to avoid those periods with zero income coming in. you'd be surprised by how many traveling professionals are willing to share a living space, to find affordable housing, especially if you'll allow pets! in my experience, allowing pets is a non-negotiable, and major perks are biweekly housekeeping (build it into the rent), and in-unit laundry. if you choose to go RBTR, here are some tips for THAT:

- designated kitchen cabinets
- designated storage space in the bathroom
- designated laundry days
- designated space in the fridge
- 'quiet hours'
- overnight guest policy (none)
- designated parking spots
- single occupancy per room

...basically all to get ahead of the quarrels between guests! we MTR our guest room in our primary (yes we share a bathroom and kitchen lol) & i've learned a lot from this experience. between that and the LTR on the other side of the duplex, it brings our mortgage from $3850 to $50, so it's worth it! i talked about this on the real estate rookie podcast & the wiire podcast - search jessie dillon in the podcast app and you'll find them!

Post: Mid Term Rental Scene in Boston?

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

hey ian! if you wanna offload this, i’d be happy to chat about doing a corporate lease with you (& running it on airbnb/vrbo on the back end). otherwise, amelia mcgee and grace just came out with a mid term rental crash course that should be good. even though travel nursing is slowing down, there are def still tons of other people looking for MTRs. you could always throw it up on furnished finder (as a prospective furnished rental) to gauge interest. 

Post: NC 10% Down Vacation Home Loan?

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

hiii i'm closing on a second/vaca home loan with 10% down on friday. milestone mortgage solutions, vernon miles 774-836-3402

Post: Cash out refinance before 6 months

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

depends on who you got the initial loan with! some don’t have a seasoning period, others require that you’re in the loan for 6mo. for example the bridge loan im in with civic financial doesn’t have a prepayment penalty, i could get out a week after closing if i wanted. 

Post: SMS/Text Marketing Legal in Massachusetts?

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

i can lend some advice for the second part of this question! with email marketing for example, a good open rate is 20%. with text, the average open rate is 90% or higher. everyone reads every text they get. that extra 10% is due to some phone carriers having a “spam text” folder. i personally have never seen this, but i do see many of my texts not being delivered due to the phone carriers’ spam folders. anywho, people rarely answer the phone, and almost always listen to voicemails. so i feel texts & voicemail drops would probably have about the same efficacy. texts might beat VM drops because they could be perceived to be more authentic (depending on how they’re written), meaning more responses. you’d also have to consider your demographic. will you know that the #s on the list are cell phones vs landlines? is your demo over a certain age, in which case, they may not be into texting or even have text-capable cell phones? things to consider! 

Post: REI Meetups in Massachusetts

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

yesss follow pints & properties new england on fb/ig! they do them monthly in worcester, lowell, rochester.. 

i just text the listing agent and ask! 

@Shawn L. thank you for your reply! so many questions.. 1. what made you target milford? 2. do you still own this property & how has it worked out? 3. how’d you originally compile that list of 1k?

as a followup to my last post: i'm interested to hear from *local* investors, what have been the most (and least) effective ways to find off-market deals in your experience? if it matters, i'm in central mass. thanks in adv!